3-[Benzyl(methyl)amino]-3-(aminocarbonyl)azetidine-1-carboxylate → Tert-butyl 3-(aminocarbonyl)-3-(methylamino)azetidine-1-carboxylate

HRID 1867740Notes

Reaction equation

HRID 1867740 reaction equation
C([N:8]([CH3:19])[C:9]1([C:16]([NH2:18])=[O:17])[CH2:12][N:11]([C:13]([O-:15])=[O:14])[CH2:10]1)C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C.C(O)C.Cl.ClCCl>[NH2:18][C:16]([C:9]1([NH:8][CH3:19])[CH2:10][N:11]([C:13]([O:15][C:9]([CH3:16])([CH3:12])[CH3:10])=[O:14])[CH2:12]1)=[O:17]

Participants

8

Reactant 2

HCID 866169493-[Benzyl(methyl)amino]-3-(aminocarbonyl)azetidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 69050638Tert-butyl 3-(aminocarbonyl)-3-(methylamino)azetidine-1-carboxylateYield 186.1%

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 3-[benzyl(methyl)amino]-3-(aminocarbonyl)azetidine-1-carboxylate (500 mg, 1.57 mmol) in ethanol (45 ml). After addition of a few drops of saturated hydrogen chloride in dichloromethane, the reaction mixture was stirred at room temperature under 2 bars of hydrogen for 3 hours. Filtration of the catalyst and concentration under reduced pressure afforded tert-butyl 3-(aminocarbonyl)-3-(methylamino)azetidine-1-carboxylate (335 mg, 93%) as a white solid; 1H NMR Spectrum: (CDCl3) 1.44 (s, 9H), 2.35 (s, 3H), 3.71 (d, 2H), 4.29 (brd, 2H), 5.51 (brs, 1H), 6.95 (brs, 1H).

Workup

  1. filtrationFiltration of the catalyst and concentration under reduced pressure

Sources & evidence

ORD record
ord-3f9670cf58d94344bba5af35598f1aa4
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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