(3S)-pyrrolidin-3-ol → (3S)-1-[3-nitro-5-(trifluoromethyl)benzyl]pyrrolidin-3-ol

HRID 1640160Notes

Reaction equation

HRID 1640160 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.Br[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-:21])=[O:20])[CH:10]=1>C(Cl)Cl>[N+:19]([C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=1)[CH2:8][N:4]1[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 2733874(3S)-pyrrolidin-3-olHCID 186217851-(Bromomethyl)-3-nitro-5-(trifluoromethyl)benzene

Product 1

HCID 58902380(3S)-1-[3-nitro-5-(trifluoromethyl)benzyl]pyrrolidin-3-olYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (S)-3-hydroxypyrrolidine (1.84 g, 21 mmol) in DCM (10 mL) at 0° C. was added a solution of 1-(bromomethyl)-3-nitro-5-(trifluoromethyl)benzene (2.00 g, 7 mmol) in DCM (10 mL) dropwise. After the addition, the reaction mixture was allowed to stir at rt for 2 h and then diluted with DCM and washed with brine. Removal of solvent gave (3S)-1-[3-nitro-5-(trifluoromethyl)benzyl]pyrrolidin-3-ol (2.25 g, 100% yield) as yellow oil. LCMS: (FA) ES+ 291.3.Step 2: 3-[((3S)-3-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidin-1-yl)methyl]-5-(trifluoromethyl)aniline

Workup

  1. additionAfter the addition
  2. washwashed with brine
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-8f04411647ab4d19bffcdb5d74393f7f
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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