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

HRID 639115Notes

Reaction equation

HRID 639115 reaction equation
[CH:1]([CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)=O.[CH3:15][NH2:16]>CO.C(Cl)Cl>[CH3:15][NH:16][CH2:1][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 4692112(+-)-1-(tert-Butoxycarbonyl)pyrrolidine-3-carboxaldehyde

Product 1

HCID 53249193tert-Butyl 3-[(methylamino)methyl]pyrrolidine-1-carboxylateYield 95.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-formyl-1-pyrrolidinecarboxylate (500 mg, 2.51 mmol) in MeOH/DCM (6 mL, 1:1) were added NaHCO (1.05 g, 12.6 mmol) followed by methylamine (2.51 mL, 5.02 mmol, 2.0 M in MeOH). After 12 h at 25° C., NaBH (1.05 g, 12.6 mmol) was added. After 1 h, the reaction was concentrated and the residue was partitioned between DCM and H O. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried over MgSO4, concentrated and purified via column chromatography (silica, 4% MeOH in DCM (1% NH OH)) yielding the title compound (512 mg, 95%) as a brown oil: LC/MS (ES) m/e 215 (M+H).

Workup

  1. waitAfter 1 h
  2. concentrationthe reaction was concentrated
  3. customthe residue was partitioned between DCM and H O
  4. extractionThe aqueous phase was extracted several times with DCM
  5. dry with materialthe combined organic fractions were dried over MgSO4
  6. concentrationconcentrated
  7. custompurified via column chromatography (silica, 4% MeOH in DCM (1% NH OH))

Sources & evidence

ORD record
ord-de235bcefe184607ad9016899eea7ac1
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

Loading…