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[ CAS No. 77-55-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 77-55-4
Chemical Structure| 77-55-4
Chemical Structure| 77-55-4
Structure of 77-55-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 77-55-4 ]

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Product Details of [ 77-55-4 ]

CAS No. :77-55-4 MDL No. :MFCD00001372
Formula : C12H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RHPCYZLXNNRRMB-UHFFFAOYSA-N
M.W : 190.24 Pubchem ID :66167
Synonyms :

Calculated chemistry of [ 77-55-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.98
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 2.81
Log Po/w (WLOGP) : 2.58
Log Po/w (MLOGP) : 2.47
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.202 mg/ml ; 0.00106 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.107 mg/ml ; 0.000562 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.15
Solubility : 0.135 mg/ml ; 0.000708 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 77-55-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 77-55-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 77-55-4 ]

[ 77-55-4 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 1932-03-2 ]
  • [ 77-55-4 ]
  • [ 24158-54-1 ]
  • 2
  • [ 77-55-4 ]
  • [ 64-17-5 ]
  • [ 4535-95-9 ]
  • 3
  • [ 77-55-4 ]
  • [ 17380-62-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 1h;Reflux; A solution of 1-phenyl cyclopentane carboxylic acid (2 g, 10.5 mmol) in thionyl chloride (20 ml) is heated to reflux for 1 hour after which time all of the starting acid has been consumed. The reaction mixture is concentrated in vacuo and the resulting acid chloride used directly for the synthesis [(tert-butoxy)carbonyl]amino 1-phenylcyclopentane-1-carboxylate, which is prepared from the described acid chloride and N-tert-butoxycarbonyl hydroxylamine according to Scheme 1. (2.4 g, 75%), 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 7.62 (1H, s), 7.18-7.49 (5H, m), 2.63-2.86 (2H, m), 1.93-2.11 (2H, m), 1.71-1.90 (4H, m), 1.45 (9H, s).
  • 4
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentanecarboxylic acid <i>p</i>-toluidide [ No CAS ]
  • 6
  • [ 21573-69-3 ]
  • [ 77-55-4 ]
YieldReaction ConditionsOperation in experiment
91% With potassium sulfite; copper(l) chloride; potassium bromide; In cyclohexane; at 160℃; for 8h; A reaction vessel equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel was charged with 230 ml of a 40% sodium bisulfite solution, 0.15 mol of stannous chloride, a stirring speed of 160 rpm, raise the solution temperature to 55 C, slowly add phenylacetaldehyde (2) 0.63mol, 1,4-diaminobutane (4) 0.73mol, dropping time control in 3h, raising the temperature of the solution to 65 C, stirring the reaction for 9h, add the mass fraction of 20% potassium bromide solution 230ml, reduce the solution temperature to 15 C, precipitation of oily liquid, for the intermediate product (3); The intermediate product (3) was washed 9 times with a mass fraction of 65%, The oil was added to 300 ml of a 45% cyclohexane solution, adding potassium bromide solution 130ml, cuprous chloride0.23 mol, potassium Sulfite 0.26mo 1, raise the solution temperature to 160 C, reflux 8 h, add 2L mass fraction of 15% sodium chloride solution, molecular sieve bleaching, hot filter, The filtrate was added with a mass fraction of 35% oxalic acid to adjust the pH of the solution to 2, Precipitation of white solid, suction filtration, sodium sulfate solution washing, the mass fraction of 75% toluene washing, activated alumina dehydration, recrystallization in nitromethane, crystal 1-phenylcyclopentanecarboxylic acid 108.93g, the yield of 91%
  • 7
  • [ 77-55-4 ]
  • [ 141-43-5 ]
  • 1-phenyl-cyclopentanecarboxylic acid-(2-diethylamino-ethylamide) [ No CAS ]
  • 8
  • [ 77-55-4 ]
  • [ 100-35-6 ]
  • [ 77-22-5 ]
  • 9
  • [ 77-55-4 ]
  • [ 615-36-1 ]
  • 1-phenyl-cyclopentanecarboxylic acid-(2-bromo-anilide) [ No CAS ]
  • 10
  • [ 110-52-1 ]
  • [ 16537-09-0 ]
  • [ 77-55-4 ]
  • 11
  • [ 64-18-6 ]
  • [ 10487-96-4 ]
  • [ 77-55-4 ]
  • 12
  • [ 77-55-4 ]
  • [ 44747-21-9 ]
  • [ 74-88-4 ]
  • [ 29885-29-8 ]
  • 13
  • [ 110-91-8 ]
  • [ 77-55-4 ]
  • [ 76277-98-0 ]
  • 14
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • [ 4535-96-0 ]
YieldReaction ConditionsOperation in experiment
sulfuric acid;Heating / reflux; To a solution of methyl [1- (2-FLUOROPHENYL) CYCLOPENTANECARBOXYLIC] acid [(LOG,] 52.56 mmol) in anhydrous methanol was added 1 mL of the concentration of sulfuric acid. The mixture was refluxed for overnight. The mixture was neutralized to pH 4-5 with sodium carbonate. The solvent was evaporated. The residue was dissolved in ethyl acetate [(50] mL), washed with brine (3 x 10 mL), dried over [MGS04.] The crude product was used for the next reaction without further purification.
  • 16
  • [ 77-55-4 ]
  • [ 37517-78-5 ]
  • [ 154382-30-6 ]
  • 17
  • [ 77-55-4 ]
  • [ 114955-85-0 ]
  • (S)-1-(4-Methoxy-3-methyl-benzyl)-5-(1-phenyl-cyclopentanecarbonyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester [ No CAS ]
  • 19
  • 1-Methyl-1-(1-phenyl-cyclopentanecarbonyloxymethyl)-pyrrolidinium; chloride [ No CAS ]
  • [ 77-55-4 ]
  • 20
  • [ 77-55-4 ]
  • [ 59115-90-1 ]
YieldReaction ConditionsOperation in experiment
93% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 18h;Reflux; To a stirred solution of 1-phenylcyclo-1-pentane-carboxylic acid (5.00 g, 26.3 mmol) in 25 mL of THF at 0C was added LAH (52 mL , 52 mmol, 1M) in THF. The reaction mixture was slowly warmed to rt and then refluxed for 18 h. The reaction was quenched according to the Fieser procedure: careful addition of 2 mL of water; 6 mL of 15% NaOH in water; and 2 mL of water. The biphasic mixture was diluted with 100 mL of ether and the granular white solid filtered off. The ether fraction was dried over Na2SO4 and evaporated to give 4.30 g (93%) of the Step 1 compound.
YieldReaction ConditionsOperation in experiment
REFERENCE EXAMPLE 19 In a stream of argon, 60% sodium hydride was dissolved in 10 ml of tetrahydrofuran, and the solution was mixed with 2.0 g of benzyl cyanide, stirred for 1 hour at room temperature, further mixed with 3.69 g of 1,4-dibromobutane and again stirred for 16 hours at room temperature. The reaction mixture was mixed with water and ethyl acetate, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography, and the resulting hexane elude was mixed with 45 ml of sulfuric acid and subjected to 24 hours of heating under reflux. After cooling down to room temperature, the reaction solution was mixed with ice water and ethyl acetate to separate water layer which was subsequently mixed with concentrated hydrochloric acid and ethyl acetate, and the resulting organic layer was separated, washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. By removing the solvent by distillation under a reduced pressure, 978 mg of 1-phenylcyclopentanecarboxylic acid was obtained. Physicochemical properties 1 H-NMR (delta ppm in CDCl3, TMS internal standard): 1.84-2.08 (m, 8H), 7.21-7.45 (m, 4H) MS (EI): 190 (M+)
REFERENCE EXAMPLE 20 Using 2.0 g of benzyl cyanide and 3.9 g of 1,5-dibromopentane, the procedure of Reference Example 19 was repeated to obtain 980 mg of 1-phenylcyclopentane-carboxylic acid. Physicochemical properties 1 H-NMR (delta ppm in CDCl3, TMS internal standard): 1.26-1.87 (m, 10H), 7.22-7.52 (m, 4H) MS (EI): 204 (M+)
  • 25
  • [ 77-55-4 ]
  • [ 31076-84-3 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(4-Acetyl-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
  • 26
  • [ 77-55-4 ]
  • [ 4659-45-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(2,6-Dichloro-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
  • 27
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • [ 31076-84-3 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(4-Acetyl-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
  • 28
  • [ 77-55-4 ]
  • [ 14002-51-8 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-[(Biphenyl-4-carbonyl)-amino]-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
  • 29
  • [ 77-55-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • [ 33863-86-4 ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(4-Butoxy-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
  • 30
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • [ 4659-45-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(2,6-Dichloro-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
  • 31
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • [ 14002-51-8 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-[(Biphenyl-4-carbonyl)-amino]-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
  • 32
  • [ 25054-53-9 ]
  • [ 77-55-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-[(Benzo[1,3]dioxole-5-carbonyl)-amino]-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
  • 33
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • [ 33863-86-4 ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(4-Butoxy-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
  • 34
  • [ 67-56-1 ]
  • [ 25054-53-9 ]
  • [ 77-55-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-[(Benzo[1,3]dioxole-5-carbonyl)-amino]-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
  • 35
  • [ 77-55-4 ]
  • [ 81677-60-3 ]
  • [ 220880-33-1 ]
  • 36
  • [ 77-55-4 ]
  • [ 423774-22-5 ]
  • 9-(3,5-dideoxy-3-[(1-phenylcyclopentyl)carbonyl]amino}-β-D-xylofuranosyl)-N6-cyclopentyladenine [ No CAS ]
  • 37
  • [ 77-55-4 ]
  • [ 225528-11-0 ]
  • (S)-3-(2'-Methoxy-biphenyl-4-yl)-2-[(1-phenyl-cyclopentanecarbonyl)-amino]-propionic acid [ No CAS ]
  • 38
  • [ 77-55-4 ]
  • [ 100-51-6 ]
  • 1-phenyl-cyclopentanecarboxylic acid benzyl ester [ No CAS ]
  • 39
  • [ 77-55-4 ]
  • [ 455311-42-9 ]
  • (+)-KF4 [ No CAS ]
  • 40
  • [ 77-55-4 ]
  • [ 444904-20-5 ]
  • (1R,4S,5S,7R)-(-)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicylo-[3.3.1]non-7-yl-(1-phenyl-1-cyclopentane)carboxamide [ No CAS ]
  • 41
  • [ 77-55-4 ]
  • (1SR,4RS,5RS,7SR)-(+/-)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicylo-[3.3.1]nonan-7-amine [ No CAS ]
  • (1SR,4RS,5RS,7SR)-(+/-)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicylo-[3.3.1]non-7-yl-(1-phenyl-1-cyclopentane)carboxamide [ No CAS ]
  • 42
  • N-(3-phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline [ No CAS ]
  • [ 77-55-4 ]
  • 1-phenylcyclopentanecarboxylic acid [4a-(3-methoxyphenyl)-8a-methyl-2-(3-phenylpropyl)octahydroisoquinolin-6-yl]amide [ No CAS ]
  • 43
  • [ 77-55-4 ]
  • [ 252002-18-9 ]
  • C28H36N2O [ No CAS ]
  • 44
  • [ 77-55-4 ]
  • [ 95-54-5 ]
  • 1-phenylcyclopentanecarboxylic acid (2-aminophenyl)amide [ No CAS ]
  • 45
  • [ 186581-53-3 ]
  • [ 77-55-4 ]
  • [ 4535-96-0 ]
  • 46
  • (+)-(1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-amine [ No CAS ]
  • [ 77-55-4 ]
  • N-[(1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]non-7-yl]-1-phenylcyclopentanecarboxamide [ No CAS ]
  • 47
  • [ 911422-98-5 ]
  • [ 77-55-4 ]
  • [ 911423-02-4 ]
  • 48
  • [ 77-55-4 ]
  • N-[(1S,4R,5R,7S)-5-(3-hydroxyphenyl)-4-methyl-2-azabicyclo[3.3.1]non-7-yl]-1-phenyl-1-cyclopentacarboxamide [ No CAS ]
  • 49
  • [ 77-55-4 ]
  • (+)-N-[(1S,4R,5R,7S)-5-(3-hydroxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]non-7-yl]-1-phenyl-1-cyclopentanecarboxamide [ No CAS ]
  • 50
  • [ 77-55-4 ]
  • (+)-N-{(1S,4R,5R,7S)-5-(3-hydroxyphenyl)-4-methyl-2-[3-(2-methylphenyl)prop-2-en-1-yl]-2-azabicyclo[3.3.1]non-7-yl}-1-phenylcyclopentanecarboxamide [ No CAS ]
  • 51
  • [ 77-55-4 ]
  • 2-(1-phenyl-cyclopentyl)-4,5-dihydro-1<i>H</i>-imidazole [ No CAS ]
  • 52
  • [ 77-55-4 ]
  • 2-(1-phenyl-cyclopentyl)-1<i>H</i>-benzoimidazole [ No CAS ]
  • 53
  • [ 77-55-4 ]
  • [ 874895-84-8 ]
  • 54
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-o-tolylcyclopentyl)oxazoline [ No CAS ]
  • 55
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-(2-ethylphenyl)cyclopentyl)oxazoline [ No CAS ]
  • 56
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-(2-propylphenyl)cyclopentyl)oxazoline [ No CAS ]
  • 57
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-(2-butylphenyl)cyclopentyl)oxazoline [ No CAS ]
  • 58
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-(2-octylphenyl)cyclopentyl)oxazoline [ No CAS ]
  • 59
  • [ 77-55-4 ]
  • 1-phenylcyclopentanecarboxylic acid 2-[1-(3,5-bis(1-methylethoxy)phenyl)-3-ethyl-7-methoxyisoquinolin-6-yloxy]ethyl ester [ No CAS ]
  • 60
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • [ 91640-63-0 ]
  • 61
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • [ 135569-28-7 ]
  • 62
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • 1-(4-Iodo-phenyl)-cyclopentanecarbonyl chloride [ No CAS ]
  • 63
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • [ 135569-31-2 ]
  • 64
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • [ 95424-44-5 ]
  • 65
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • 20(4-phenylpiperidinyl)ethyl 1-phenylcyclopentanecarboxylate [ No CAS ]
  • 66
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • 2-(4-phenylpiperazinyl)ethyl 1-phenylcyclopentanecarboxylate [ No CAS ]
  • 67
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • 1-Phenyl-cyclopentanecarboxylic acid 3-(4-phenyl-piperidin-1-yl)-propyl ester [ No CAS ]
  • 71
  • [ 77-55-4 ]
  • [ 80606-91-3 ]
  • 72
  • [ 77-55-4 ]
  • [ 80606-01-5 ]
  • 73
  • [ 77-55-4 ]
  • [ 136089-22-0 ]
  • 74
  • [ 77-55-4 ]
  • [ 136089-15-1 ]
  • 75
  • [ 77-55-4 ]
  • [ 136089-24-2 ]
  • 76
  • [ 77-55-4 ]
  • [ 136089-20-8 ]
  • 83
  • [ 77-55-4 ]
  • 2-hydroxy-1,2-bis-(1-phenyl-cyclopentyl)-ethanone [ No CAS ]
  • 84
  • [ 77-55-4 ]
  • [ 68580-51-8 ]
  • 85
  • [ 77-55-4 ]
  • [ 17380-74-4 ]
YieldReaction ConditionsOperation in experiment
61% To a solution of carboxylic acid (1.5 g, 7.89 mmol) in H20/acetone (1: 10/12 mL total) at 0C was added Et3N (1.43 mL, 10.3 mmol) followed by addition of ethyl chloroformate (0.83 mL, 8.68 mmol). The resulting mixture was stirred for 30 min after which a solution of NaN3 (0.77g, 11. 8 mmol) in H20 (2 mL) was added dropwise. The resultant heterogenous mixture was stirred for 1 h at 0C, then cold water (5 mL) and Et20 (10 mL) were added. The layers were separated and the aqueous layer was extracted with Et20 (2 x 10 mL). The organic layers were combined, toluene (20 mL) was added, and the organic layers were dried (MgS04) and concentrated under reduced pressure to a volume of 20 mL. t-BuOH (5 mL) was added and the mixture was refluxed for 12h. The mixture was concentrated under reduced pressure and the crude residue was taken up in 3M HCI (30 mL) and was heated at reflux for 12h. The mixture was cooled to room temperature and extracted with Et20 (3 x 15 mL). The aqueous layer wa s cooled to 0 C and solid NaOH pellets were added until pH-12 was reached. The aqueous layer was extracted with Et20 (3 x 30 mL) and the combined organic layers were dried (MgS04) and concentrated under reduced pressure to afford 0.78 g (61 % yield) of an oil [MH+ 162]. This material was used without further purification.
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