Methylamine → (R)-tert-butyl 3-((R)-(3-chlorophenyl)(3-(methylamino)-3-oxopropoxy)methyl)piperidine-1-carboxylate

HRID 451666Notes

Reaction equation

HRID 451666 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:22][CH2:23][CH2:24][C:25]([O:27]CC)=O)[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[CH3:30][NH2:31]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:22][CH2:23][CH2:24][C:25]([NH:31][CH3:30])=[O:27])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59201378(3R)-tert-butyl 3-((3-chlorophenyl)(3-ethoxy-3-oxopropoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 59201651(R)-tert-butyl 3-((R)-(3-chlorophenyl)(3-(methylamino)-3-oxopropoxy)methyl)piperidine-1-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3R)-tert-butyl 3-((3-chlorophenyl)(3-ethoxy-3-oxopropoxy)methyl)piperidine-1-carboxylate (2.0 g, 4.71 mmol) was dissolved in a solution CH3NH2 in CH3OH ((180 mL) and stirred overnight at rt. After the reaction was complete by HPLC analysis, the solvent was removed in vacuo. The residue was purified by preparative HPLC and afforded the desired isomerically pure product (R)-tert-butyl 3-((R)-(3-chlorophenyl)(3-(methylamino)-3-oxopropoxy)methyl)piperidine-1-carboxylate (0.80 g, 1.95 mmol, 41% yield). MS (E/Z): 411 (M+H+).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by preparative HPLC
  3. customafforded the

Sources & evidence

ORD record
ord-2d19726a42604c6ea9abcb9cd43389dc
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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