Sodium borohydride → HCID 57887027, compound

HRID 1798779Notes

Reaction equation

HRID 1798779 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. LC/MS: 4.72 min; z/e 535, calcd (M+1) 535. 1H NMR (400 MHz: CDCl3): 7.55 (2H), 6.95 (2H), 3.85-3.55 (3H), 3.30 (1H minor), 3.00 (1H major), 2.80 (1H), 2.65 (1H), 2.55 (1H major), 2.50 (1H minor), 1.95-1.65 (4H), 1.45 (9H), 0.90 (9H), 0.5 (6H).

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-1a35492887d543f6a1ae5558c28c292b
Source dataset
uspto-grants-2013_01
Patent number
US08343986B2

Reaction notes

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