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Chemical Structure| 239483-09-1 Chemical Structure| 239483-09-1

Structure of 239483-09-1

Chemical Structure| 239483-09-1

(S)-tert-Butyl 2-(2-aminoethyl)pyrrolidine-1-carboxylate

CAS No.: 239483-09-1

4.5 *For Research Use Only !

Cat. No.: A132709 Purity: 95%

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Product Details of [ 239483-09-1 ]

CAS No. :239483-09-1
Formula : C11H22N2O2
M.W : 214.31
SMILES Code : O=C(N1[C@H](CCN)CCC1)OC(C)(C)C
MDL No. :MFCD04115291
InChI Key :VCYKQOGWPICUKV-VIFPVBQESA-N
Pubchem ID :7016511

Safety of [ 239483-09-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 239483-09-1 ]

* 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 [ 239483-09-1 ]

[ 239483-09-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 142253-50-7 ]
  • [ 239483-09-1 ]
YieldReaction ConditionsOperation in experiment
80% With ammonia; hydrogen;dihydrogen hexachloroplatinate; nickel; In methanol; water; under 2068.65 Torr; for 24h; Step d 2S-(2-Aminoethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester. The product of step c (1.45 g, 6.9 mmol) was suspended in methanol saturated with ammonia (50 ml), Raney-Nickel (ca. 1.0 g) and hydrogen hexachloroplatinate (IV) hydrate (80 mg dissolved in I ml of water) were added. The mixture was stirred in a Parr bottle under H2 pressure (about 40 psi) for 24 h. The reaction mixture was filtered through Celite and the filtrate was evaporated. The crude material was purified by flash chromatography (DCM:methanol:amonia (880) 90:10:1) to afford the title compound (1.18g, 80%). 1H NMR 3.90 (1H, m), 3.30 (2H, m), 2.71 (2H, t), 1.87-1.45 (17H, m).
50% With ammonia; hydrogen;Raney-Ni; In ethanol; water; under 2585.81 Torr; d) -V-BOC-(2S)-2-(2-Aminoethyl)-1-pyrrolidinc. A solution of NBOC- EPO <DP n="136"/>(2S) -2-cyano-1 -pyrrolidine (179 mg, 0.85 mmol) in ethanol saturated with anhydrousammonia was treated with Raney-Ni (1 mL of 50% aq. Suspension) and 50 psi of Hsovernight, The mixture was filtered through Cclitc and the filtrate was concentratedan vacuo. The residue was purified by flash chromatography (10% CH3OH/CH2CI2with 1% NH-iOH gradient elution) through a short plug of silica gel to give -7V-BOC-(2S)-2-(2-aminoethyl)-1-pyrrohdmo (90 mg, 50%) as a clear oil. 1H NMRexists as rotomers (CDCl3) delta 3.88-3,77 (m, 1 H), 3.33-3.24 (m, 2 H), 2.66 (m, 2 H),1.89- 1.54 (m, 6 H), 1.40 (s, 9 H),
With ammonia; hydrogen;nickel; In methanol; for 14h; a: Borane dimethylsulfide, THF, 14 h, RT b: METHANESULFONYLCHLORIDE, triethylamine, dichloromethane, 4 h, RT c: Sodium cyanide, DIMETHYLFORMAMIDE, 5 h, RT d: Raney nickel, ammonia gas in methanol, H2 2. 5 kg pressure, 14 h e: 1/ 1-methyl cinnamaldehyde, dichloromethane, 16 H, RT, N2 2/Sodium borohydride, methanol, 30 minutes at 0C Scheme 2: Preparation OF2- [2- (2-METHYL-3-PHENYL-ALLYLAMINO)-ETHYL- (S)-PYRROLIDINE-L-CARBOXYLIC acid tert-butyl ester [00138] Compound 2- [2- (2-Methyl-3-phenyl-allylamino)-ethyl- (S)- PYRROLIDINE-1-CARBOXYLIC acid tert-butyl ester (prepared from (S)-Pyrrolidine- 1, 2-DICARBOXYLIC ACID-1-TERT-BUTYL ester according to the scheme 2) 0.47 g (1.3 MMOL) and 3,4, 5-trimethoxy benzoic acid 0.3 g (1.6 MMOL) in dry dichloromethane 10ml, triethyl amine 0.1 ml was added and stirred at room temperature for 20 min. Then 1-DIMETHYLAMINOPROPYL-3-ETHYL CARBODIIMIDE 0.3 g (2 MMOL) and 1-hydroxybenzotriazole 0.018 g (0.13 MMOL) was added at 0C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and was washed with 10% sodium bicarbonate solution, water and brine, dried, concentrated and subjected to column chromatography (silica gel, n-hexane: ethylacetate as eluent) to yield 0.57 g 2-{2-[(2-METHYL-3-PHENYL-ALLYL)-3, 4,5-trimethoxy- BENZOYL)-AMINO]-ETHYL}-(S)-PYRROLIDINE-1-CARBOXYLIC acid tert-butyl ester (Yield : 76%). The compound 0.22 g (0.4 MMOL) was dissolved in 5ML of dry ether and 5ML of dry ether saturated with HCI was added at 0C. The reaction mixture was stirred at room temperature for 10 hrs. The ether was concentrated and the residue was washed with dry ether three to four times to yield 0.12 g as a white solid. Yield : 30%. [00139] LC-MSD, m/z for C26H34N204 [M+H] +: 439.3 [00140] 1H NMR (300 MHz, MeOD) : 8 1. 6-1.8 (m, 4 H), 2.0-2. 25 (m, 6H), 3.3-3. 5 (m, 3H), 3.2 (m, 3H), 3.5-4. 0 (m, 12H), 4.1 (s, 1H), 6.5 (s, 1H), 6.8-7. 0 (m, 2H), 7.2-7. 5 (m, 5H).
 

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