1-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(methoxycarbonyl)amino]ethoxy]methyl]-, 1,1-dimethylethyl ester, (3R)- → HCID 58017419, compound

HRID 452004Notes

Reaction equation

HRID 452004 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C@H:8]([O:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH3:29])=[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.[H][H]>CO.[OH-].[OH-].[Pd+2]>[CH3:29][O:28][C:26]([NH:25][CH2:24][CH2:23][O:22][C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1)[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:10]1)=[O:27]

Participants

5

Reactant 2

HCID 595984981-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(methoxycarbonyl)amino]ethoxy]methyl]-, 1,1-dimethylethyl ester, (3R)-HCID 178418361HCID 178418361, compound

Product 1

HCID 58017419HCID 58017419, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate (3 g, 7.04 mmol) in MeOH (60 mL) was added wet Pd(OH)2/C (300 mg). The reaction mixture was stirred under 50 of hydrogen psi at 50° C. for 3 hr. The suspension was filtered and the filtrate was concentrated hydrogen in vacuo. The crude product was purified by preparative HPLC to afford (R)-tert-butyl 3-((R)-(2-(methoxycarbonylamino)ethoxy)(phenyl)methyl)piperidine-1-carboxylate (1.4 g, 51%). 1H NMR (CD3OD) δ 7.40-7.22 (m, 5H), 4.20 (m, 1H), 4.01 (m, 1H), 3.81 (m, 1H), 3.6 (s, 3H), 3.27 (m, 3H), 2.84 (m, 2H), 1.8-1.5 (m, 2H), 1.45 (s, 9H). MS ESI +ve m/z 393 (M+1).

Workup

  1. filtrationThe suspension was filtered
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-a51451dfea04489d89b1f3611e7e7ed9
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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