Triethylamine → tert-Butyl (2S,5R)-2-ethyl-5-methylpiperazine-1-carboxylate

HRID 251840Notes

Reaction equation

HRID 251840 reaction equation
C(O)(=O)C.[C:5]([N:12]1[CH2:17][C@@H:16]([CH3:18])[NH:15][CH2:14][C@@H:13]1[CH2:19][CH3:20])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(CC)CC)C>ClCCl>[C:5]([N:12]1[CH2:17][C@@H:16]([CH3:18])[NH:15][CH2:14][C@@H:13]1[CH2:19][CH3:20])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 66841763906810-51-3

Product 1

HCID 29944002tert-Butyl (2S,5R)-2-ethyl-5-methylpiperazine-1-carboxylateYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Boc-2(S)-ethyl-5(R)-methylpiperazine acetic acid salt (10 g) was dissolved in dichloromethane (100 mL) and treated with triethylamine (4 mL, 3 g). Solvent was evaporated and the residue was passed through a silica gel column, eluting with 3% methanol (containing ammonia) in dichloromethane, to give 1-Boc-2(S)-ethyl-5(R)-methylpiperazine free base (7.2 g).

Workup

  1. customSolvent was evaporated
  2. washeluting with 3% methanol (containing ammonia) in dichloromethane

Sources & evidence

ORD record
ord-3c593123445e4e4ebe5e3cd08bad85fe
Source dataset
uspto-grants-2011_01
Patent number
US07868006B2

Reaction notes

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