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Chemical Structure| 180683-64-1 Chemical Structure| 180683-64-1
Chemical Structure| 180683-64-1

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Product Details of tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate

CAS No. :180683-64-1
Formula : C11H22N2O2
M.W : 214.30
SMILES Code : O=C(OC(C)(C)C)N[C@@H]1[C@@H](N)CCCC1
MDL No. :MFCD08460986
InChI Key :AKVIZYGPJIWKOS-IUCAKERBSA-N
Pubchem ID :1514391

Safety of tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3259
Packing Group:

Application In Synthesis of tert-Butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate

* 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 [ 180683-64-1 ]

[ 180683-64-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 4755-77-5 ]
  • [ 180683-64-1 ]
  • [ 910117-05-4 ]
  • 2
  • [ 180683-64-1 ]
  • {(1S,2S)-2-[((S)-4-Isopropyl-4,5-dihydro-oxazole-2-carbonyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester [ No CAS ]
  • 3
  • [ 180683-64-1 ]
  • {(1S,2S)-2-[((S)-1-Hydroxymethyl-2-methyl-propylaminooxalyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester [ No CAS ]
  • 4
  • [ 180683-64-1 ]
  • Toluene-4-sulfonic acid (S)-2-[((1S,2S)-2-tert-butoxycarbonylamino-cyclohexylaminooxalyl)-amino]-3-methyl-butyl ester [ No CAS ]
  • 5
  • [ 180683-64-1 ]
  • 3-((E)-Styryl)-octahydro-quinoxalin-2-one [ No CAS ]
  • 6
  • [ 180683-64-1 ]
  • C54H73N9O2 [ No CAS ]
  • 7
  • [ 180683-64-1 ]
  • [[2-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid [ No CAS ]
  • 8
  • [ 180683-64-1 ]
  • [ 193621-93-1 ]
  • 9
  • [ 180683-64-1 ]
  • [[2-(6-Benzyloxycarbonylamino-purin-9-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid [ No CAS ]
  • 10
  • [ 180683-64-1 ]
  • [ 193621-92-0 ]
  • 11
  • [ 180683-64-1 ]
  • [[2-(2-Benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid [ No CAS ]
  • 12
  • [ 180683-64-1 ]
  • [ 193621-94-2 ]
  • 13
  • [ 180683-64-1 ]
  • [ 180509-99-3 ]
  • 14
  • [ 180683-64-1 ]
  • N-(2S-Boc-aminocyclohex-1S-yl)-N-(thymin-1-ylacetyl)-glycine [ No CAS ]
  • 15
  • [ 24424-99-5 ]
  • [ 180683-64-1 ]
YieldReaction ConditionsOperation in experiment
In chloroform; The mono-Boc amines were synthesised from the commercially available diamines using a literature procedure (10 equiv. of diamine and 1 equiv. of Boc2O in chloroform followed by an aqueous work up to remove unreacted diamine) (34). N-tert-butoxycarbonyl-1,6-trans-diaminocyclohexane. Mp 159-161 C.; 1H NMR (CDCl3) delta 4.35 (br s, 1H), 3.37 (br s, 1H), 2.61 (br s, 1H), 1.92-2.02 (m, 2H), 1.81-1.89 (m, 2H), 1.43 (s, 9H), 1.07-1.24 (m, 4H) ppm; 13C NMR (D6-DMSO) delta 154.9, 77.3, 49.7, 48.9, 35.1, 31.4, 28.3 ppm; ES-MS (M+1) calcd 215.17, found 215.22.
In chloroform; The mono-Boc amines were synthesised from the commercially available diamines using a literature procedure (10 equiv. of diamine and 1 equiv. of Boc2O in chloroform followed by an aqueous work up to remove unreacted diamine) (34). N-tert-butoxycarbonyl-1,6-trans-diaminocyclohexane. Mp 159-161 C.; 1H NMR (CDCl3) delta 4.35 (br s, 1H), 3.37 (br s, 1H), 2.61 (br s, 1H), 1.92-2.02 (m, 2H), 1.81-1.89 (m, 2H), 1.43 (s, 9H), 1.07-1.24 (m, 4H) ppm; 13C NMR (D6-DMSO) delta 154.9, 77.3, 49.7, 48.9, 35.1, 31.4, 28.3 ppm; ES-MS (M+1) calcd 215.17, found 215.22.
YieldReaction ConditionsOperation in experiment
The following compounds were produced by the method similar to that in Reference Example 1. ... N-tert-Butoxycarbonyl-1,7-heptanediamine N-tert-Butoxycarbonyl-1,8-octanediamine N-tert-Butoxycarbonylpiperazine cis-N-tert-Butoxycarbonyl-1,2-cyclohexanediamine trans-N-tert-Butoxycarbonyl-1,2-cyclohexanediamine cis-N-tert-Butoxycarbonyl-1,3-cyclohexanediamine trans-N-tert-Butoxycarbonyl-1,3-cyclohexanediamine cis-N-tert-Butoxycarbonyl-1,4-cyclohexanediamine ...
  • 17
  • [ 96-32-2 ]
  • [ 180683-64-1 ]
  • N-(2S-Boc-aminocyclohex-1S-yl)-glycine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.9 g (70%) With potassium carbonate; In N,N-dimethyl-formamide; EXAMPLE 2 N-(2S-Boc-aminocyclohex-1S-yl)-glycine, methyl ester (2) To a cooled suspension of 1 (2 g, 9.35 mmol) and potassium carbonate (3.87 g, 28.05 mmol) in DMF (15 ml) was added a solution of methyl bromoacetate (0.9 ml, 9.35 mmol) in DMF (5 ml) over a period of 5 min. After one hour at 0 C. the salts were filtered and washed with DMF and CH2 Cl2. The filtrate was evaporated under reduced pressure and the residue was purified by chromatography on silica gel (eluent ethylacetate). Yield: 1.9 g (70%). mp: 68-70 C.; NMR1 H (dmso d6) ppm: 1.0-1.3 (m,4H,2CH2 cycl); 1.45 (s, 9H, t-Boc); 1.4-2.0 (m,5H,2CH2 cycl+NH); 2.3 (dt, 1H, CHN); 3.1 (m, 1H, CHN); 3.4 (dt, 2H, CH2 COO); 3.7 (s, 3H, COOCH3); 6.7 (m, 1H, NH carbamate); NMR 13 C (dmso d6) ppm: 172.9 (ester); 155.5 (carbamate); 77.5 (t-Boc); 59.7, 47.6 (CH2 COOCH3); 53.7, 51.4, 32.1, 31.1, 24.6, 24.2 (C cyl); 28.3 (t-Boc); MSFAB+: 287.0 (M+1).
  • 18
  • (-)-(1R,2R)-diaminocyclohexane [ No CAS ]
  • [ 24424-99-5 ]
  • [ 180683-64-1 ]
YieldReaction ConditionsOperation in experiment
73% In dichloromethane; water; EXAMPLE 1 (1S,2S)-1-(N-t-butyloxycarbonylamino)-2-aminocyclohexane (1) To a cooled solution of (1S,2S)-diaminocyclohexane (5 ml; 41.6 mmol) in CH2 Cl2 (25 ml) was added a solution of di-t-butyl dicarbonate (3.03 g; 13.9 mmol) in CH2 Cl2 (25 ml) over a period of 30 mins. The reaction mixture was stirred overnight at room temperature. Water (20 ml) and CH2 Cl2 (25 ml) were added in order to dissolve the precipitate. After separation of the two phases, the organic phase was concentrated under reduced pressure and the residue was dissolved in ether (25 ml) and water (25 ml). The mixture was acidified to pH 5 with HCl 4N and the bis-protected diamine was extracted with ether (3*25 ml). The aqueous phase was adjusted to 10.5 with NaOH 2N and extracted with ethylacetate (6*30 ml). The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure to yield the title-compound (2.3 g, 73% based on Boc2 O).
  • 19
  • [ 180683-64-1 ]
  • N-[(R)-2-amino-3-(p-nitrophenyl)propyl]-trans-(S,S)-cyclohexane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
N-[(R)-2-Amino-3-(p-nitrophenyl)propyl]-trans-(S,S)-cyclohexane-l,2-diamine was previously generally prepared in accordance with Wu, C, Kobayashi, H., Sun, B., Yoo, T. M., Paik, C. H., Gansow, O. A., Carrasquillo, J. A., Pastan, L, Brechbiel, M. W.: Stereochemical Influence on the Stability of Radio-Metal Complexes In Vivo. Synthesis and Evaluation of the Four Stereoisomers of 2-(p-nitrobenzyl)-trans-CyDTPA. Bioorg. Med. Chem. 1997, 5, 1925-1934. However, the procedure was modified in that the intermediate monoprotected 2,2-diaminocyclohexane was prepared according to a higher yielding route taken from Young. K. Kim, Seok J. Lee and Kyo H.Ahn: New hybrid ligands with a trans- 1,2-diaminocyclohexane backbone: competing chelation modes in palladium-catalysed enantioselective allylic alkylation. J. Org Chem. 2000, 65, 7807-7813.
  • 20
  • [ 880644-81-5 ]
  • [ 180683-64-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; N-[(R)-2-Amino-3-(p-nitrophenyl)propyl]-trans-(S,S)-cyclohexane-l,2-diamine was previously generally prepared in accordance with Wu, C, Kobayashi, H., Sun, B., Yoo, T. M., Paik, C. H., Gansow, O. A., Carrasquillo, J. A., Pastan, L, Brechbiel, M. W.: Stereochemical Influence on the Stability of Radio-Metal Complexes In Vivo. Synthesis and Evaluation of the Four Stereoisomers of 2-(p-nitrobenzyl)-trans-CyDTPA. Bioorg. Med. Chem. 1997, 5, 1925-1934. However, the procedure was modified in that the intermediate monoprotected 2,2-diaminocyclohexane was prepared according to a higher yielding route taken from Young. K. Kim, Seok J. Lee and Kyo H.Ahn: New hybrid ligands with a trans- 1,2-diaminocyclohexane backbone: competing chelation modes in palladium-catalysed enantioselective allylic alkylation. J. Org Chem. 2000, 65, 7807-7813.
  • 21
  • [ 180683-64-1 ]
  • (+/-)-trans-N-[(5-Methyl-4,5,6,7-tetrahydrothiazolo [5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
[Referential Example 50] (+-)-trans-N-[(5-Methyl-4,5,6,7-tetrahydrothiazolo [5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride: The title compound was obtained from (+-)-trans-N-tert-butoxycarbonyl-1,2-cyclohexanediamine in a similar manner to Referential Example 37. 1H-NMR (DMSO-d6) delta: 1.10-2.17(8H,m), 2.92(3H,s), 3.00-3.93(6H,m), 4.38-4.60(1H,m), 4.64-4.77(1H,m), 8.00-8.19(3H,m), 8.82-8.96(1H,m) 11.95-11.30(1H,m). MS (FAB) m/z: 295(M+H)+.
  • 22
  • [ 21436-03-3 ]
  • [ 180683-64-1 ]
YieldReaction ConditionsOperation in experiment
[Referential Example 39] (+-)-trans-N-tert-Butoxycarbonyl-1,2-cyclohexanediamine: The title compound was obtained from (+-)-trans-1,2-cyclohexanediamine in a similar manner to Referential Example 34. mp 79-81C. 1H-NMR (CDCl3) delta: 1.05-1.34(4H,m), 1.45(9H,s), 1.68-1.75(2H,m), 1.92-2.02(2H,m), 2.32(1H,dt,J=10.3,3.9Hz), 3.08-3.20(1H,m), 4.50(1H,br.s). MS (FAB) m/z: 215(M+H)+.
  • 23
  • [ 17794-48-8 ]
  • [ 180683-64-1 ]
  • [ 445478-72-8 ]
  • 24
  • [ 58632-95-4 ]
  • [ 21436-03-3 ]
  • [ 180683-64-1 ]
  • 25
  • [ 40138-16-7 ]
  • [ 18531-99-2 ]
  • [ 180683-64-1 ]
  • tert-butyl (E,1S,2S)-2-((2-((Sa)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaborepin-4-yl)phenyl)methylideneamino)cyclohexylcarbamate [ No CAS ]
  • 26
  • [ 947274-13-7 ]
  • [ 180683-64-1 ]
  • [ 1084793-60-1 ]
YieldReaction ConditionsOperation in experiment
tert-Butyl [ (IS, 2S) -2-aminocyclohexyl] carbamate (1.29 g) and ethyl 3-bromo-2-isocyano-3-phenylacrylate (1.4 g) were dissolved in DMF (15 ml). N,N-Diisopropylethylamine (1.29 g) was added, and the mixture was stirred at room temperature for 40 hr. DBU (761 mg) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. Saturated brine was added to the reaction mixture, and the liberated oil was extracted with ethyl acetate. The extract was washed successively with 6% aqueous sodium bicarbonate, 10% aqueous citric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and the fraction eluted with ethyl acetate- hexane (1:1 - 1:0) was concentrated under reduced pressure to give the object compound (1.24 g) .1H-NMR (CDCl3) delta 1.05-1.41 (6H, m) , 1.34 (9H, s) , 1.75-1.85 (3H, m), 2.06 (2H, t) , 3.44-3.51 (1H, m) , 3.73-3.79 (1H, m) , 4.05 (1H, s)f 4.22 (2H, q) , 7.32-7.34 (2H, m) , 7.48-7.52 (3H, m) , 7.72 (1H, S)
  • 27
  • [ 585-47-7 ]
  • [ 180683-64-1 ]
  • [ 1142953-14-7 ]
  • 28
  • [ 1190086-92-0 ]
  • [ 180683-64-1 ]
  • 29
  • [ 66-77-3 ]
  • [ 180683-64-1 ]
  • C22H28N2O2 [ No CAS ]
  • 30
  • [ 66-99-9 ]
  • [ 180683-64-1 ]
  • C22H28N2O2 [ No CAS ]
  • 31
  • [ 642-31-9 ]
  • [ 180683-64-1 ]
  • C26H30N2O2 [ No CAS ]
  • 32
  • [ 158399-19-0 ]
  • [ 180683-64-1 ]
  • C37H54N2O5 [ No CAS ]
  • 33
  • (R)-2,2'-dihydroxy-(1,1'-binaphthalene)-3,3'-dicarbonyl dichloride [ No CAS ]
  • [ 180683-64-1 ]
  • C44H54N4O8 [ No CAS ]
  • 34
  • (S)-2,2'-dihydroxy-[1,1'-binaphthyl]-3,3'-dicarbonyl dichloride [ No CAS ]
  • [ 180683-64-1 ]
  • C44H54N4O8 [ No CAS ]
  • 35
  • [ 180683-64-1 ]
  • [ 906565-55-7 ]
  • C48H78N6O6 [ No CAS ]
 

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