Water → HCID 10270089, compound

HRID 1837998Notes

Reaction equation

HRID 1837998 reaction equation
[CH3:1][N:2]1[C@@H:6]([C:7]([C:9]2[S:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)=[O:8])[C@@H:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:4][C:3]1=[O:26].[Li+].[BH4-].O>C1COCC1>[OH:8][C@@H:7]([C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)[C@@H:6]1[N:2]([CH3:1])[C:3](=[O:26])[CH2:4][C@@H:5]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 10292077HCID 10292077, compound

Product 1

HCID 10270089HCID 10270089, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (4R,5R)-1-methyl-4-phenyl-5-[(5-phenyl(2-thienyl))-carbonyl]pyrrolidin-2-one (60 mg, 0.17 mmol) in THF (2 mL) was added a solution of LiBH4 (2M in THF, 0.1 mL, 0.2 mmol) and the reaction mixture was heated at 50° C. for 2 h. The resulting pale yellow suspension was treated with water and a saturated NH4Cl solution, extracted with EtOAc, dried (Na2SO4), concentrated onto silica gel and purified by flash chromatography to give (4R,5R)-5-[(1R)-hydroxy(5-phenyl(2-thienyl))methyl]-1-methyl-4-phenylpyrrolidin-2-one (43 mg, 71%) as a yellow solid: TLC (EtOAc) Rf 0.36; HPLC ES-MS m/z 364 (MH+).

Workup

  1. extractiona saturated NH4Cl solution, extracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated onto silica gel
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-f28e78b21d8741c39468f87fb5f953bb
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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