Dimethylamine → Tert-butyl 3-(dimethylamino)azetidine-1-carboxylate

HRID 855607Notes

Reaction equation

I[CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[CH3:13][NH:14][CH3:15]>>[CH3:13][N:14]([CH3:15])[CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Product 1

HCID 23145930Tert-butyl 3-(dimethylamino)azetidine-1-carboxylate

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl 3-iodoazetidine-1-carboxylate (EP 1176147, prep 18) (5 g, 17.6 mmol) and dimethylamine (27 mL, 33% in ethanol, 176 mmol) was heated to 80° C. for 28 hours in a sealed vessel. The cooled mixture was evaporated in vacuo and the residue pre-adsorbed onto silica gel. This was then purified by column chromatography on silica gel using ethyl acetate:hexane (50:50) as eluant to afford the title compound as a yellow oil, 1.07 g.

Workup

customThe cooled mixture was evaporated in vacuo
customThis was then purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-00c471a1ee804c0dbf526302d8b1ee25
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262192B2

Reaction notes

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