Water → [1-(4-Hydroxy-cyclohexyl)-1-phenyl-ethyl]carbamic acid tert-butyl ester

HRID 45203Notes

Reaction equation

HRID 45203 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]([CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>C1COCC1>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]([CH:16]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67075684[1-(4-Oxo-cyclohexyl)-1-phenyl-ethyl]carbamic acid tert-butyl ester

Product 1

HCID 70252586[1-(4-Hydroxy-cyclohexyl)-1-phenyl-ethyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

[1-(4-Oxo-cyclohexyl)-1-phenyl-ethyl]-carbamic acid tert-butyl ester (28) from the previous stage (2.7 g) was dissolved in THF (60 mL) and cooled to −70° C. Sodium borohydride was added (356 mg) and the reaction mixture stirred overnight with gradual warming to room temperature. Water was added and the solution extracted with t-butylmethyl ether. The organic phase was washed with brine and dried over sodium sulphate. Evaporation gave 1.24 g of a white foam as crude product. Rt=1.41 min (Method 5). Detected mass: 246.3 (M—C4H8—H2O+H+).

Workup

  1. temperaturewith gradual warming to room temperature
  2. extractionthe solution extracted with t-butylmethyl ether
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. customEvaporation

Sources & evidence

ORD record
ord-185d432c8c5f4d009988d1b57e6488fa
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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