Triethylamine → 3-(Benzyloxycarbonylaminomethyl)-piperidine-1-carboxylic Acid Tert-butyl Ester

HRID 896528Notes

Reaction equation

HRID 896528 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH2:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 27564831-Boc-3-(aminomethyl)piperidine

Product 1

HCID 451587943-(Benzyloxycarbonylaminomethyl)-piperidine-1-carboxylic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-aminomethylpiperidine-1-carboxylic acid tert-butyl ester (2.20 g, 10.3 mmol) in dichloromethane (40 mL) was treated with triethylamine (1.90 mL, 13.3 mmol) and stirred on an ice bath. A solution of benzyl chloroformate (1.90 mL, 13.3 mmol) in dichloromethane (10 mL) was added over 5 minutes. The mixture was stirred at room temperature for 70 hours. It was washed with 0.1 N aqueous hydrochloric acid, dried over sodium sulfate, and concentrated under vacuum to provide a colorless gum (3.58 g, quantitative) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ7.37 (m, 5H), 5.11 (s, 2H), 3.75 (m, 2H), 3.18 (m, 1H), 3.05 (m, 2H), 2.83 (m, 1H), 1.9-1.6 (m, 4H), 1.46 (s, 9H), 1.27 (m, 1H).

Workup

  1. stirringThe mixture was stirred at room temperature for 70 hours
  2. washIt was washed with 0.1 N aqueous hydrochloric acid
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto provide a colorless gum (3.58 g, quantitative) which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-221948ae8b0e4dcc8db64c9b351ccf52
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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