Sodium borohydride → HCID 59075085, compound

HRID 2184340Notes

Reaction equation

HRID 2184340 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:34])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C@@H:17](/[CH:18]=[CH:19]/[C:20](=[O:30])[C:21]2[O:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=2)[CH2:16][C:15]([CH3:32])([CH3:31])[C:14]1=[O:33])[CH3:4]>CO>[CH2:3]([O:5][C:6](=[O:34])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C@@H:17](/[CH:18]=[CH:19]/[CH:20]([OH:30])[C:21]2[O:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=2)[CH2:16][C:15]([CH3:31])([CH3:32])[C:14]1=[O:33])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59075097HCID 59075097, compound

Product 1

HCID 59075085HCID 59075085, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (37 mg, 0.98 mmol) was slowly added to a solution of 7-{(R)-3,3-dimethyl-2-oxo-5-[(E)-3-oxo-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-pyrrolidin-1-yl}-heptanoic acid ethyl ester (280 mg, 0.61 mmol) in methanol (4 mL) at −20° C. The reaction flask was kept at −10° C. for 45 minutes. When the addition was complete the reaction vessel was kept at −10 C for 40 min. When the reaction was done, it was quenched with acetone and concentrated to dryness. The residue was dissolved in ethyl acetate, washed with brine and dried. After concentration, the crude mixture was purified on a silica gel column using hexane:ethyl acetate 1:1 as the solvent, giving 90 mg of 7-{(R)-5-[(E)-3-hydroxy-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-3,3-dimethyl-2-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester.

Workup

  1. additionWhen the addition
  2. waitwas kept at −10 C for 40 min
  3. customit was quenched with acetone
  4. concentrationconcentrated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with brine
  7. customdried
  8. concentrationAfter concentration
  9. customthe crude mixture was purified on a silica gel column

Sources & evidence

ORD record
ord-06fbb0af505442ac82307f2458a1fda3
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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