Methylamine → tert-Butyl 3-(methylamino)pyrrolidine-1-carboxylate

HRID 2365203Notes

Reaction equation

HRID 2365203 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:14][NH2:15].[BH4-].[Na+]>CO.ClCCl>[C:4]([O:3][C:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH:15][CH3:14])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 45089533tert-Butyl 3-(methylamino)pyrrolidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-N—BOC-3-pyrrolidinone (3.0 g) in methanol (30 ml) was added a solution of freshly prepared methylamine (0.75 g) in methanol (3.1 ml). The reaction mixture was stirred for 1 hour and then sodium borohydride (0.61 g) was added. After stirring for 4 hours the reaction mixture was then diluted with dichloromethane, washed with sodium bicarbonate solution, dried (MgSO4) and the solvent removed in vacuo to give 3-methylamino-pyrrolidine-1-carboxylic acid tert-butyl ester (3.18 g).

Workup

  1. stirringAfter stirring for 4 hours the reaction mixture
  2. washwashed with sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a82a8d3118ba445e927d40c03f261120
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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