Ethylamine → (3R)-tert-butyl 3-((3-chlorophenyl)(2-(ethylamino)-2-oxoethoxy)methyl)piperidine-1-carboxylate

HRID 451658Notes

Reaction equation

HRID 451658 reaction equation
[CH2:1]([NH2:3])[CH3:2].[Cl:4][C:5]1[CH:6]=[C:7]([CH:11]([O:25][CH2:26][C:27]([O:29]CC)=O)[C@@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)[CH:8]=[CH:9][CH:10]=1>>[Cl:4][C:5]1[CH:6]=[C:7]([CH:11]([O:25][CH2:26][C:27]([NH:3][CH2:1][CH3:2])=[O:29])[C@@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:13]2)[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 6341EthylamineHCID 59201743(3R)-tert-butyl 3-((3-chlorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 59201433(3R)-tert-butyl 3-((3-chlorophenyl)(2-(ethylamino)-2-oxoethoxy)methyl)piperidine-1-carboxylateYield 58%

Procedure

To a solution of EtNH2 in alcohol (30% by weight, 10 mL) was added (3R)-tert-butyl 3-((3-chlorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate (100 mg, 0.243 mmol). The mixture was stirred at rt overnight. The mixture was concentrated under vacuum to give crude product, which was purified by preparative tlc (elution solvent: 5:1 petroleum ether/EtOAc) to give (3R)-tert-butyl 3-((3-chlorophenyl)(2-(ethylamino)-2-oxoethoxy)methyl)piperidine-1-carboxylate (57.9 mg. 58%) as a colorless oil. MS (E/Z): 411 (M+H+).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customto give crude product, which
  3. customwas purified by preparative tlc (elution solvent: 5:1 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-1ba27018dea145b6af6c49a87672cf8f
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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