Sodium borohydride → [1-Methyl-1-(4-hydroxy-cyclohexyl)-ethyl]carbamic acid tert-butyl ester

HRID 45188Notes

Reaction equation

HRID 45188 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]([CH3:17])([CH:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]([CH3:9])([CH:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)[CH3:17])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67075173[1-Methyl-1-(4-oxo-cyclohexyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 67075479[1-Methyl-1-(4-hydroxy-cyclohexyl)-ethyl]carbamic acid tert-butyl esterYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.91 g of [1-Methyl-1-(4-oxo-cyclohexyl)-ethyl]-carbamic acid tert-butyl ester (20) were dissolved in 60 mL of ethanol and 473 mg of sodium borohydride were added at −20° C. The mixture was allowed to warm to room temperature and stirred for 3.5 h. The mixture was evaporated, the residue was dissolved in ethyl acetate and washed twice with 2N hydrochloric acid and once with brine. The organic layer was dried over sodium sulphate and evaporated to dryness to give 2.74 g of (21). Rt=1.27 min (Method 5). Detected mass: 194 (M-Isobutene-H2O+H+).

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed twice with 2N hydrochloric acid and once with brine
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-600573f8af644a498af9d93213a53594
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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