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

HRID 1297254Notes

Reaction equation

HRID 1297254 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8](=[O:26])[CH2:9][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:26])[CH2:9][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 58914664Tert-butyl 5-biphenyl-4-yl-3-oxopentanoate2×

Product 1

HCID 116240165-Biphenyl-4-yl-3-hydroxy-pentanoic acid tert-butyl esterYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (51 mg, 1.4 mmol) was added in one portion to a stirred solution of 5-biphenyl-4-yl-3-oxo-pentanoic acid tert-butyl ester (Intermediate 2, 400 mg, 1.23 mmol) in methanol (5 mL) at 0° C. under nitrogen. Stirring was continued for 30 mrrinutes then 1 M hydrochloric acid (5 mL) was added. The crude reaction mixture was extracted with diethyl ether (3×20 mL) and the resulting organic phases were combined, dried (MgSO4) then the solvent removed by evaporation under reduced pressure to give the title compound (375 mg, 93%) as a colourless oil. LC/MS: 3.67 min; z/e 344, calcd (M+NH4) 344.1H NMR (400 MHz: CDCl3): 7.55 (2 H), 7.50 (2 H), 7.43 (2 H), 7.38 (3 H), 4.01 (1 H), 3.25 (1 H), 2.80 (2 H), 2.44 (2 H), 1.82 (2 H), 1.45 (9 H).

Workup

  1. customThe crude reaction mixture
  2. extractionwas extracted with diethyl ether (3×20 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-15a4a15538c447949fea764727228e07
Source dataset
uspto-grants-2007_07
Patent number
US07250439B2

Reaction notes

Loading…