Dimethylformamide → Tert-butyl 3-(acetylthio)azetidine-1-carboxylate

HRID 241635Notes

Reaction equation

HRID 241635 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.C(=O)([O-])[O-].[Cs+].[Cs+].[C:19]([OH:22])(=[S:21])[CH3:20].CN(C)C=O>C(OCC)C>[C:19]([S:21][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1)(=[O:22])[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 178418634HCID 178418634, compound

Product 1

HCID 18363257Tert-butyl 3-(acetylthio)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

Mixture of tert-butyl 3-iodoazetidine-1-carboxylate (STEP B, 2.05 g, 7.24 mmol), cesium carbonate (4.72 g, 14.5 mmol), thioacetic acid (1.10 g, 14.5 mmol) and dimethyl formamide (10 mL) was stirred at 70° C. for 4 h. The reaction mixture was cooled to room temperature and diluted with diethyl ether (200 mL). The resulting mixture was washed with water (80 mL×3) and brine (50 mL), then dried over magnesium sulfate.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe resulting mixture was washed with water (80 mL×3) and brine (50 mL)
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-3500009c1b194654b46723524043a094
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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