Sodium borohydride → HCID 57887027, compound

HRID 2382919Notes

Reaction equation

HRID 2382919 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([Si:7]([CH3:31])([CH3:30])[O:8][CH2:9][CH2:10][CH:11]([C:19](=[O:29])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([I:28])=[CH:24][CH:23]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([CH3:6])[CH3:5]>CO>[CH3:6][C:4]([Si:7]([CH3:30])([CH3:31])[O:8][CH2:9][CH2:10][CH:11]([CH:19]([OH:29])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([I:28])=[CH:24][CH:23]=1)[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])([CH3:3])[CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57887028HCID 57887028, compound

Product 1

HCID 57887027HCID 57887027, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.59 g, 15.6 mmol) was added portion wise to a stirred solution of 1,1-dimethylethyl 2-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-5-(4-iodophenyl)-3-oxopentanoate (7.55 g, 14.2 mmol) in methanol (100 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 (100 mL). The resulting mixture was extracted with diethyl ether (3×200 mL) then the organic layers were combined, washed with brine (100 mL), dried (sodium sulfate) and the solvent evaporated. The residue was chromatographed on silica gel (25% to 50% diethyl ether:cyclohexane) to give the title compound (5.14 g, 68%) as a colourless oil which was a mixture of diastereomers.

Workup

  1. additionOn completion of addition
  2. customthe reaction was quenched with saturated aqueous ammonium chloride solution (100 mL)
  3. extractionThe resulting mixture was extracted with diethyl ether (3×200 mL)
  4. washwashed with brine (100 mL)
  5. dry with materialdried (sodium sulfate)
  6. customthe solvent evaporated
  7. customThe residue was chromatographed on silica gel (25% to 50% diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-743f92521828471ab1a9f99ae33ce27c
Source dataset
uspto-grants-2012_09
Patent number
US08263602B2

Reaction notes

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