Triethylsilane → HCID 63585886, compound

HRID 1931883Notes

Reaction equation

HRID 1931883 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[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]=[C:18]([F:20])[CH:17]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 19935801HCID 19935801, compound

Product 1

HCID 63585886HCID 63585886, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (−)-1-benzyl-3-(3,5-difluorophenyl)pyrrolidin-3-ol (2.73 g, 9.44 mmol), methanol (20 mL) and palladium on carbon (500 mg) was purged with nitrogen. Triethyl silane (15.09 mL, 94.4 mmol) was added drop wise over 3 h and the mixture was stirred at ambient temperature for 24 h. The mixture was filtrated over celite, evaporated and purified by flash chromatography on silica gel (ethyl acetate/methanol/triethylamine, 1:0 to 0:4:1) to give the title compound (1.4 g). MS m/z (relative intensity, 70 eV) 199 (M+, bp), 141, (50), 127 (58), 114 (50), 113 (71).

Workup

  1. customwas purged with nitrogen
  2. filtrationThe mixture was filtrated over celite
  3. customevaporated
  4. custompurified by flash chromatography on silica gel (ethyl acetate/methanol/triethylamine, 1:0 to 0:4:1)

Sources & evidence

ORD record
ord-bc70c624f5244ad7ae70b41df9456406
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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