Ethanol → HCID 11054718, compound

HRID 253561Notes

Reaction equation

HRID 253561 reaction equation
Cl[CH2:2][C@H:3]([OH:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CCO>[OH-].[Na+].O>[CH:6]1([CH2:5][C@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@@H:3]2[CH2:2][O:20]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 702EthanolHCID 57462030tert-Butyl (2S,3R)-4-chloro-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate

Product 1

HCID 11054718HCID 11054718, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

tert-Butyl (2S,3R)-4-chloro-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (1 g, 3.28 mmol) was dissolved in a solution of 0.7 N NaOH in EtOH (5.6 mL, 3.95 mmol, 1.2 eq). After stirring for 1 h, the mixture was concentrated to give the residue, which was dissolved in water, extracted with EtOAc (3×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give tert-butyl (S)-2-cyclohexyl-1-((R)-oxiran-2-yl)ethylcarbamate (0.83 g, 95%). 1H NMR: 0.85 (m, 1H), 0.99 (m, 1H), 1.12-1.32 (m, 3H), 1.41 (m, 3H), 1.45 (s, 9H), 1.58 (m, 4H), 1.88 (m, 1H), 2.59 (m, 1H), 2.73 (m, 1H), 2.98 (m, 1H), 4.04 (m, 1H), 4.32 (m, 1H). MS (E/Z): 270 (M+H+).

Workup

  1. concentrationthe mixture was concentrated
  2. customto give the residue, which
  3. extractionextracted with EtOAc (3×15 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-292f1e5922c9484ea635f15374e27979
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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