Sodium borohydride → HCID 57887021, compound

HRID 2382914Notes

Reaction equation

HRID 2382914 reaction equation
[BH4-].[Na+].[C:3]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=[O:30])[CH:12]([CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:5][CH:4]=1>CO>[C:3]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([OH:30])[CH:12]([CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:24])[CH3:25])[C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57887031tert-Butyl 5-biphenyl-4-yl-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopentanoate

Product 1

HCID 57887021HCID 57887021, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.05 g, 27.7 mmol) was added portion wise to a stirred solution of tert-butyl 5-biphenyl-4-yl-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopentanoate (12.1 g, 25.2 mmol) in methanol (80 mL) at 0° C. under nitrogen. On completion of addition stirring was continued for 1.5 h then the reaction was quenched with saturated aqueous ammonium chloride solution (80 mL). The resulting mixture was extracted with diethyl ether (3×200 mL) then the organic layers were combined, washed with brine (100 mL), dried (magnesium sulfate) and the solvent evaporated. The residue was chromatographed on silica gel (10% to 50% diethyl ether:cyclohexane) to give the title compound (8.47 g, 69%) as a colourless oil which was a mixture of diastereomers. LC/MS: 4.49 min; z/e 485, calcd (M+1) 485. 1H NMR (400 MHz: CDCl3): 7.60 (2H), 7.50 (2H), 7.45 (2H), 3.90 (1H minor), 3.80 (1H minor), 3.70 (1H major), 3.65 (1H major), 3.25 (1H minor), 3.00 (1H major), 2.90 (1H), 2.75 (1H), 2.60 (1H major), 2.55 (1H minor), 1.90 (1H), 1.85 (2H), 1.45 (10H), 0.90 (9H), 0.5 (6H).

Workup

  1. additionOn completion of addition
  2. customthe reaction was quenched with saturated aqueous ammonium chloride solution (80 mL)
  3. extractionThe resulting mixture was extracted with diethyl ether (3×200 mL)
  4. washwashed with brine (100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent evaporated
  7. customThe residue was chromatographed on silica gel (10% to 50% diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-23fb93ac36fe427f8acaa56a6eb97b67
Source dataset
uspto-grants-2012_09
Patent number
US08263602B2

Reaction notes

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