Triethylsilane → HCID 63585886, compound

HRID 1931873Notes

Reaction equation

HRID 1931873 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 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (+)-1-benzyl-3-(3,5-difluorophenyl)pyrrolidin-3-ol (0.853 g, 2.95 mmol), methanol (15 mL) and palladium on carbon (170 mg) was purged with nitrogen. Triethyl silane (3.42 g, 29.5 mmol) was added in 7 equal portions over 3.5 h and the resulting mixture was stirred at ambient temperature for 3 h. The mixture was filtrated over celite, evaporated and Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) gave the title compound (0.53 g). MS m/z (relative intensity, 70 eV) 199 (M+, bp), 141, (61), 127 (73), 114 (59), 113 (88).

Workup

  1. customwas purged with nitrogen
  2. filtrationThe mixture was filtrated over celite
  3. customevaporated
  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-1ef73446d49c48dfbc892e6ae641b618
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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