Sodium borohydride → HCID 69547774, compound

HRID 2184330Notes

Reaction equation

HRID 2184330 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@@H:12]1/[CH:17]=[CH:18]/[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([O:36][CH3:37])([O:34][CH3:35])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1)=[O:20])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:38])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@@H:12]1/[CH:17]=[CH:18]/[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([O:34][CH3:35])([O:36][CH3:37])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]=1)[OH:20])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59075098HCID 59075098, compound

Product 1

HCID 69547774HCID 69547774, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (5 mL) of 7-((R)-2-{(E)-3-[3-(dimethoxy-phenyl-methyl)-phenyl]-3-oxo-propenyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester (124 mg, 0.24 mmol)was added NaBH4 (36 mg, 0.96 mmol). The reaction mixture was stirred for 2.25 h and then concentrated to dryness. The residue was dissolved in ethyl acetate and washed with NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated to provide 7-((R)-2-{(E)-3-[3-(dimethoxy-phenyl-methyl)-phenyl]-3-hydroxy-propenyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester. To a methanol solution (5 mL) of 7-((R)-2-{(E)-3-[3-(dimethoxy-phenyl-methyl-phenyl]-3-hydroxy-propenyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid ethyl ester was added an aqueous solution (2.5 mL) of LiOH monohydrate (46 mg, 1.09 mmol). The reaction mixture was stirred for 6 h and then concentrated to remove the methanol. The aqueous concentrate was diluted with CH2Cl2 and 1 N HCl was added, extracted with CH2Cl2 and dried over MgSO4. This mixture was filtered and concentrated to yield 7-((R)-2-{(E)-3-[3-(dimethoxy-phenyl-methyl)-phenyl]-3-hydroxy-propenyl}-5-oxo-pyrrolidin-1-yl)-heptanoic acid (116 mg, 0.23 mmol) as an oil.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9fd11ec1117b46d0ae5c1d5859b951a5
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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