Ammonium Hydroxide → tert-butyl (2S,3S)-4-amino-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate

HRID 253568Notes

Reaction equation

HRID 253568 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@@H:9]2[CH2:11][O:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[NH4+:21]>CO>[NH2:21][CH2:11][C@H:9]([OH:10])[C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 11054718HCID 11054718, compound

Product 1

HCID 14179444tert-butyl (2S,3S)-4-amino-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl (S)-2-cyclohexyl-1-((R)-oxiran-2-yl)ethylcarbamate (0.20 g, 0.74 mmol) in MeOH (15 mL) at rt, ammonium hydroxide (5 mL) was added. The resulting clear solution was stirred at rt overnight, and completion of reaction was confirmed by LC-MS. Solvent was removed under vacuum to leave tert-butyl (2S,3S)-4-amino-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (0.21 g, quant.), which was used for the next step without purification; M/S m/z 287 (M+H+).

Workup

  1. customcompletion of reaction
  2. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-4c5ca48973f04b52a10cc1c58b6bb278
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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