Sodium borohydride → HCID 58675134, compound

HRID 1297260Notes

Reaction equation

HRID 1297260 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8](=[O:21])[CH2:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=1)([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8](=[O:21])[CH2:9][CH:10]([OH:20])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([I:19])=[CH:17][CH:18]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58914663HCID 58914663, compound2×

Product 1

HCID 58675134HCID 58675134, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (198 mg, 5.20 mmol) was added in one portion to a stirred solution of 5-(4-iodo-phenyl)-3-oxo-pentanoic acid tert-butyl ester (Intermediate 8, 1.78 g, 4.76 mmol) in methanol (15 mL) at 0° C. The reaction was stirred for 20 minutes then quenched with 1 M HCl (15 mL). The resulting mixture was extracted with diethyl ether (3×20 mL). The organic phases were combined, dried (MgSO4) then the solvent removed by evaporation under reduced pressure to give the title compound (1.46 g, 82%) as a colourless oil. LC/MS: 3.59 min; z/e 394, calcd (M+NH4) 394. 1H NMR (400 MHz: CDCl3): 7.6 (2 H), 6.95 (2 H), 3.95 (1 H), 2.7 (2 H), 2.38 (2 H), 1.73 (2 H), 1.45 (9 H).

Workup

  1. customthen quenched with 1 M HCl (15 mL)
  2. extractionThe resulting mixture was 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-a4f721cf04d8486296fd4717c1c04427
Source dataset
uspto-grants-2007_07
Patent number
US07250439B2

Reaction notes

Loading…