Triethylsilane → 3-(3,4-Difluorophenyl)pyrrolidin-3-ol

HRID 1931872Notes

Reaction equation

HRID 1931872 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)([OH:13])[CH2:9]1)C1C=CC=CC=1.C([SiH](CC)CC)C>[Pd].CO>[F:21][C:16]1[CH:15]=[C:14]([C:10]2([OH:13])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:19]=[CH:18][C:17]=1[F:20]

Participants

5

Reactant 2

HCID 12052Triethylsilane2×HCID 671736601-Benzyl-3-(3,4-difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 635869723-(3,4-Difluorophenyl)pyrrolidin-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent2×

Procedure

Preparation according to Preparation 18: Enantiomer E2 of 1-benzyl-3-(3,4-difluorophenyl)pyrrolidin-3-ol (0.835 g, 2.89 mmol), methanol (15 mL), palladium on carbon (165 mg), triethyl silane (6.7 g, 57.7 mmol). Reaction restart: Methanol (15 mL), palladium on carbon (165 mg), triethyl silane (6.7 g, 57.7 mmol). Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine 4:1). Yield: 0.54 g. MS m/z (relative intensity, 70 eV) 199 (M+, 85), 141, (bp), 127 (58), 114 (53), 113 (98).

Workup

  1. customPreparation
  2. customaccording to Preparation 18
  3. customReaction restart
  4. customPurification
  5. washon a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine 4:1)

Sources & evidence

ORD record
ord-e51348bac6bb480fb3853affdc0c8529
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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