HCID 70026212, compound → HCID 45090954, compound

HRID 396298Notes

Reaction equation

HRID 396298 reaction equation
C([N:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15](=[O:17])[CH3:16])[C@H:10]([CH3:18])[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[C:15]([O:14][C@H:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH3:18])(=[O:17])[CH3:16]

Participants

4

Reactant 1

HCID 70026212HCID 70026212, compound

Product 1

HCID 45090954HCID 45090954, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of cis-1-benzyl-4-(RS)-acetoxy-3-(SR)-methylpiperidine [7 g, 28.5 mmole {prepared according to literature procedure described in A. F. Casy and W. K. Jeffery, Can.J.Chem., 50 (1972), 803}] and 20% palladium hydroxide (1.8 g) in methanol (25 ml) was stirred at 50-55° C. under hydrogen (1 atmosphere) for 20 hr. The catalyst was filtered off and washed with methanol. Filtrate was concentrated to give cis-4-(RS)-acetoxy-3-(SR)-methylpiperidine as oil. Yield 4.4 g (99%), C8H15NO2, m/z 158 (M+1), PMR (CDCl3): 0.94 (3H, d, CH3, j=8 Hz), 1.42 (1H, m, H3), 1.67 (1H, m, H5), 1.98 (1H, m, H5), 2.08 (3H, s, COCH3), 2.31 (1H, t, H2, j=12 Hz), 2.68 (1H, dt, H2, j=3 Hz, 12 Hz), 3.04 (2H, m, H6), 4.95 (1H, d, H4, j=6 Hz).

Workup

  1. customprepared
  2. filtrationThe catalyst was filtered off
  3. washwashed with methanol
  4. concentrationFiltrate was concentrated

Sources & evidence

ORD record
ord-100fe6099ada429dba79caa59b6c1d3b
Source dataset
uspto-grants-2003_08
Patent number
US06608078B2

Reaction notes

Loading…