(R)-tert-butyl 3-((R)-(3-chlorophenyl)(3-(methylamino)-3-oxopropoxy)methyl)piperidine-1-carboxylate → 3-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)-N-methylpropanamide

HRID 451667Notes

Reaction equation

HRID 451667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:22][CH2:23][CH2:24][C:25]([NH:27][CH3:28])=[O:26])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:6][CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[O:22][CH2:23][CH2:24][C:25]([NH:27][CH3:28])=[O:26])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59201651(R)-tert-butyl 3-((R)-(3-chlorophenyl)(3-(methylamino)-3-oxopropoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 592016203-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)-N-methylpropanamideYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(3-(methylamino)-3-oxopropoxy)methyl)piperidine-1-carboxylate (0.80 g, 1.95 mmol) was dissolved in a 20% solution of TFA in CH2Cl2 (20.6 mL) and stirred for about 1 h at rt until the reaction was complete. The solvent was removed by evaporation and the crude product was purified with preparative HPLC to afford 3-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)-N-methylpropanamide (542 mg, 1.75 mmol, 90% yield). MS (E/Z): 311 (M+H+).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe crude product was purified with preparative HPLC

Sources & evidence

ORD record
ord-83f51e9f8be94110bf4b14d91f9451ef
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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