Hydrochloric Acid → tert-Butyl (2S)-2-methylpiperazine-1-carboxylate

HRID 38296Notes

Reaction equation

HRID 38296 reaction equation
Cl.[CH3:2][N:3]([CH:11]1[CH2:15][CH2:14][N:13](S(C2C=CC=CC=2)(=O)=O)[CH2:12]1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])O.[Na+]>C(O)C>[CH3:7][C:6]([O:5][C:4]([N:3]1[CH2:2][CH2:14][NH:13][CH2:12][C@@H:11]1[CH3:15])=[O:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86631067methyl[1-(phenylsulfonyl)-3-pyrrolidinyl]-carbamic Acid, 1,1-dimethylethyl Ester

Product 1

HCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M HCl (50 ml) was added drop wise to a solution of the product of part (b) (31.8 g) in ethanol (1500 ml), the reaction was stirred for 1.5 h. Solid sodium hydrogen carbonate (8.4 g) was added and stirred for 1 h, then concentrated in vacuo. The residue was purified by chromatography (silica, 0-2-5% MeOH/DCM as eluent) to remove the by-products, then eluted with 10% MeOH/DCM to give the sub-title compound (9.3 g).

Workup

  1. stirringstirred for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography (silica, 0-2-5% MeOH/DCM as eluent)
  4. customto remove the by-products
  5. washeluted with 10% MeOH/DCM

Sources & evidence

ORD record
ord-be11fc2e8a46465a937c0ea2836b069d
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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