4-Benzyl-4-piperidinol → (RS)-4-Benzyl-1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-hydroxy-propyl}-piperidin-4-ol

HRID 1419929Notes

Reaction equation

HRID 1419929 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]2[CH2:16][O:15]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([C:26]1([OH:32])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH2:19]([C:26]1([OH:32])[CH2:31][CH2:30][N:29]([CH2:16][CH:14]([OH:15])[CH2:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:18])[CH3:17])=[CH:8][CH:9]=2)[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 981524-Benzyl-4-piperidinolHCID 54376003(RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silane

Product 1

HCID 70045791(RS)-4-Benzyl-1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-hydroxy-propyl}-piperidin-4-olYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silane (0.62 g, 2.34 mmol) was dissolved in MeOH (8 ml) and stirred overnight at room temperature in the presence of 4-benzyl-4-hydroxy-piperidine (0.9 g, 4.68 mmol). The reaction mixture was concentrated and the residue was chromatographed over silica gel (hexane-ethylacetate 1:1, then CH2Cl2 --MeOH 19:1) to provide (RS)-4-Benzyl-1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-hydroxy-propyl}-piperidin-4-ol (0.95 g, 90%) as a yellow oil, MS: m/e=456.5 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was chromatographed over silica gel (hexane-ethylacetate 1:1

Sources & evidence

ORD record
ord-604a34fa4db04c1d8b16c7fd84c195c1
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

Loading…