Tert-butyl 3-[benzyl(methyl)amino]-3-[(methylamino)carbonyl]azetidine-1-carboxylate → Tert-butyl 3-(methylamino)-3-[(methylamino)carbonyl]azetidine-1-carboxylate

HRID 1867770Notes

Reaction equation

HRID 1867770 reaction equation
[CH2:1]([N:8](C)[C:9]1([C:20]([NH:22][CH3:23])=[O:21])[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1)C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C.C(O)C.Cl.ClCCl>[CH3:1][NH:8][C:9]1([C:20]([NH:22][CH3:23])=[O:21])[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12]1

Participants

8

Reactant 2

HCID 69050278Tert-butyl 3-[benzyl(methyl)amino]-3-[(methylamino)carbonyl]azetidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 69050792Tert-butyl 3-(methylamino)-3-[(methylamino)carbonyl]azetidine-1-carboxylateYield 93.3%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% wt Palladium on charcoal (160 mg) in ethyl acetate (2 ml) was added to a solution of tert-butyl 3-[benzyl(methyl)amino]-3-[(methylamino)carbonyl]azetidine-1-carboxylate (580 mg, 1.74 mmol) in ethanol (45 ml). After the addition of a few drops of saturated hydrogen chloride in dichloromethane, the reaction mixture was stirred at room temperature under 3 bars of hydrogen for 3 hours. Filtration of the catalyst and concentration under reduced pressure gave tert-butyl 3-(methylamino)-3-[(methylamino)carbonyl]azetidine-1-carboxylate (395 mg, 93%) as a white solid, which was used without further purification in the next step. 1H NMR Spectrum: (CDCl3) 1.43 (s, 9H), 2.30 (s, 3H), 2.84 (s, 3H), 3.68 (d, 2H), 4.27 (brs, 2H), 7.05 (brs, 1H).

Workup

  1. filtrationFiltration of the catalyst and concentration under reduced pressure

Sources & evidence

ORD record
ord-95722e5ad747434db1c070972adcf674
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

Loading…