HCID 131725707, compound → HCID 131725708, compound

HRID 1796793Notes

Reaction equation

HRID 1796793 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]=[CH:21][C:20]([CH3:25])([OH:24])[CH:19]2[C:26]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:27][SiH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].CO>[C:29]([SiH2:28][O:27][C:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH:19]1[C:20]([CH3:25])([OH:24])[CH2:21][CH2:22][CH2:23][N:18]1[S:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)(=[O:16])=[O:17])([CH3:30])([CH3:31])[CH3:32]

Participants

5

Reactant 2

HCID 131725707HCID 131725707, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 131725708HCID 131725708, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(4-benzyloxy-benzenesulfonyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-methyl-1,2,3,6-tetrahydro-pyridin-3-ol (compound of formula VIII, 0.40 g, 0.64 mmol), 10% palladium on charcoal (0.1 g) and 30 ml of methanol was stirred for about 16 hours under about 1 atmosphere of hydrogen gas. The mixture was filtered through a pad of Celite®. Concentration of the filtrate afforded 0.35 g of 2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(4-hydroxy-benzenesulfonyl)-3-methyl-piperidin-3-ol (compound of formula IX) as a colorless solid.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®

Sources & evidence

ORD record
ord-5a1bc679244b4ee3b49fb1ebee789501
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

Loading…