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

HRID 645976Notes

Reaction equation

HRID 645976 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, Step 2) 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-1859f03b69ce4bf5bb5e4320782f2240
Source dataset
uspto-grants-2010_04
Patent number
US07705020B2

Reaction notes

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