Hydrochloric Acid → 5-Biphenyl-4-yl-3-hydroxy-2-methyl-pentanoic acid tert-butyl ester

HRID 1297258Notes

Reaction equation

HRID 1297258 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8](=[O:27])[CH:9]([CH3:26])[C:10](=[O:25])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].Cl>CO>[C:3]([O:7][C:8](=[O:27])[CH:9]([CH3:26])[CH:10]([OH:25])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17][CH:18]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 586751335-Biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester2×

Product 1

HCID 586751285-Biphenyl-4-yl-3-hydroxy-2-methyl-pentanoic acid tert-butyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (17 mg, 0.44 mmol) was added to a stirred solution of 5-biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester (Intermediate 6, 135 mg, 0.399 mmol) in methanol (3 mL) at 0° C. under nitrogen. After stirring for 1 hour 1 M hydrochloric acid (5 mL) was added and the crude reaction mixture extracted with diethyl ether (3×5 mL). The organic phases were combined, washed with brine (5 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure to give the title compound (130 mg, 96%) as a colourless gum, mixture of diastereoisomers. LC/MS: 3.72 min; z/e 341, calcd (M+1) 341.1H NMR (400 MHz: CDCl3): 7.59 (2 H), 7.51 (2 H), 7.42 (2 H), 7.28 (3 H), 4.21, 3.90, 3.65, 2.89, 2.75, 1.81, 1.69, 1.55, 1.44, 1.30, 1.18.

Workup

  1. additionwas added
  2. customthe crude reaction mixture
  3. extractionextracted with diethyl ether (3×5 mL)
  4. washwashed with brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. customThe volatiles were removed by evaporation under reduced pressure
  7. customto give

Sources & evidence

ORD record
ord-f12dad23b44444f9b72c38b8b74b5046
Source dataset
uspto-grants-2007_07
Patent number
US07250439B2

Reaction notes

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