Water → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-1-(3-hydroxymethylphenyl)-pyrrolidin-2-one

HRID 1819361Notes

Reaction equation

HRID 1819361 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[CH:17]=3)[CH2:13][C:12]2=[O:30])[CH:6]=1)C.[BH4-].[Na+].O>CCO>[CH:25]1([O:24][C:18]2[CH:17]=[C:16]([CH:14]3[CH2:15][N:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][OH:3])[CH:6]=4)[C:12](=[O:30])[CH2:13]3)[CH:21]=[CH:20][C:19]=2[O:22][CH3:23])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 962Water2×HCID 4311764Sodium borohydrideHCID 688284533-[4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzoic acid ethyl ester

Product 1

HCID 688290524-(3-Cyclopentyloxy-4-methoxyphenyl)-1-(3-hydroxymethylphenyl)-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]benzoic acid ethyl ester (20 mg, 0.05 mmol) in EtOH (0.5 mL) was added NaBH4 (5 mg, 0.135 mmol)). The mixture was stirred at r.t. for 12 h when water (1 mL) was added to quench the reaction. The mixture was poured into water (4 mL) and extracted twice with EtOAc. The combined organic layer was concentrated and purified by preparative LC-MS.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionextracted twice with EtOAc
  5. concentrationThe combined organic layer was concentrated
  6. custompurified by preparative LC-MS

Sources & evidence

ORD record
ord-017644f7dc0141c79f2ea3ddd1d4aa2b
Source dataset
uspto-grants-2009_10
Patent number
US07601742B2

Reaction notes

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