Sodium borohydride → HCID 178453609, compound

HRID 271363Notes

Reaction equation

HRID 271363 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([C@@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[OH:10][CH:9]([C@@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:13][CH2:12]1)[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178453608HCID 178453608, compound

Product 1

HCID 178453609HCID 178453609, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl {[cis-4-(3-phenylpropanoyl)cyclohexyl]-methyl]carbamate (3.45 g, 10.0 mmol) in ethanol (65 ml) under nitrogen cooled in an ice-bath was added sodium borohydride (0.78 g, 21 mmol). The mixture was stirred two hours at ice-bath temperature. The reaction was quenched by addition saturated sodium bicarbonate solution (30 ml). The mixture was concentrated under reduced pressure to remove ethanol. The aqueous residue was diluted with water (15 ml) and extracted with ethyl acetate (3×60 ml). The extract was washed with water (20 ml), and brine (20 ml), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give crude (±)-tert-butyl {[cis-4-(1-hydroxy-3-phenylpropyl)cyclohexyl]methyl)carbamate (3.64 g, theoretical yield 3.48 g) as a colorless gum. MS: 348.3 (M+1).

Workup

  1. customThe reaction was quenched by addition saturated sodium bicarbonate solution (30 ml)
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto remove ethanol
  4. additionThe aqueous residue was diluted with water (15 ml)
  5. extractionextracted with ethyl acetate (3×60 ml)
  6. washThe extract was washed with water (20 ml), and brine (20 ml)
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-7d7c9208d543451882bbb6f3c6aa040e
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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