(3S,4S)-Methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate → (3S,4R)-4-(4-Chloro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl ester

HRID 2305569Notes

Reaction equation

HRID 2305569 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][C@H:9]2[C:15]([O:17][CH3:18])=[O:16])=[CH:4][CH:3]=1>CCOCC.CCN(CC)CC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][C@H:9]2[C:15]([O:17][CH3:18])=[O:16])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 10355644(3S,4S)-Methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate

Product 1

HCID 12972672(3S,4R)-4-(4-Chloro-phenyl)-1-methyl-piperidine-3-carboxylic acid methyl esterYield 18%

Reagents, catalysts & solvents 1

HCID 22234951Ether triethylamineSolvent

Procedure

Concentration of the mother liquor from Example 1 gave a mixture of compounds 1 and 2. Flash chromatography on silica gel using ether/Et3N 9/1 as eluent gave compound 2 (2.0 g, 18%): 1H NMR (benzene-d6) δ—1.4-1.5 (m, 1H),—1.62 (dq, 1H, J=3.9 and 12.6 Hz), 1.75 (dt, 1H, J=2.7 and 12.0 Hz), 2.06 (s, 3H), 2.0-2.15 (m, 1H), 2.54-2.63 (m, 1H), 2.68 (dt, 1H, J=4.2 and 11.7 Hz), 2.86-3.0 (m, 2H), 3.08 (s, 3H), 6.87 (d, 2H, J=8.7 Hz), 7.07 (d, 2H), J=8.7 Hz); 13C NMR (CDCl3) δ 33.1, 44.0, 46.1, 49.1, 51.5, 55.7, 58.1, 128.6, 128.7, 132.3, 141.9, 173.4; MS m/z (%) 267 (M+, 17), 208 (30), 128 (16), 114 (16), 43 (100).

Workup

  1. customConcentration of the mother liquor from Example 1 gave

Sources & evidence

ORD record
ord-1fdd329e35ca40d0aa546e7351d42ce3
Source dataset
uspto-grants-2002_08
Patent number
US06440996B1

Reaction notes

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