9-Borabicyclo(3.3.1)nonane → (R)-1-[4-(4-chlorophenoxy)phenyl]-2-[3-(trifluoromethyl)phenyl]pyrrolidine

HRID 1972240Notes

Reaction equation

HRID 1972240 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][CH2:15][C:14]3=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.B1C2CCCC1CCC2>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:14][CH2:15][CH2:16][C@@H:17]3[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=3)=[CH:9][CH:8]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 59485681(R)-1-[4-(4-chlorophenoxy)phenyl]-5-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one

Product 1

HCID 59485613(R)-1-[4-(4-chlorophenoxy)phenyl]-2-[3-(trifluoromethyl)phenyl]pyrrolidineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-1-[4-(4-chlorophenoxy)phenyl]-5-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one (6.4 mg, 0.015 mmol), THF (0.5 mL) and 9-BBN (0.5 M in hexane, 0.5 mL) is stirred at room temperature overnight. After concentration, the residue is purified on silica gel (0-30% ethyl acetate in hexane) to give the title compound (5.1 mg, 82%) as a colorless oil. HPLC-MS calculated for C23H19ClF3NO (M+H+) 418.11, found 418.10.

Workup

  1. concentrationAfter concentration
  2. customthe residue is purified on silica gel (0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c925db0778aa486399f19a65bbdbd8fa
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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