Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate → Methyl 1-{[4-(aminomethyl)piperidin-1-yl]methyl}cyclopentanecarboxylate

HRID 736414Notes

Reaction equation

HRID 736414 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1)=O)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 67232469Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate

Product 1

HCID 67232206Methyl 1-{[4-(aminomethyl)piperidin-1-yl]methyl}cyclopentanecarboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate (1.16 g, 3.27 mmol, Step2) in CH2Cl2 (25 mL) and trifluoroacetic acid (5 mL) was stirred at room temperature for 1.5 h. The reaction mixture was then concentrated and basified with sat. NaHCO3 aq. (100 mL), extracted with CHCl3 (100 mL) for five times. The combined extract was dried and concentrated to give 0.831 g (100%) of title compound as yellow syrup.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. extractionextracted with CHCl3 (100 mL) for five times
  3. extractionThe combined extract
  4. customwas dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6cf6402b7d914d99b4956daa63b0e016
Source dataset
uspto-grants-2009_09
Patent number
US07595329B2

Reaction notes

Loading…