Tetrahydrofuran → tert-Butyl 3-acetylazetidine-1-carboxylate

HRID 1873853Notes

Reaction equation

HRID 1873853 reaction equation
CON(C)[C:4]([CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5].O1CCC[CH2:19]1.O1CCCC1.C[Mg]Cl>CCOCC>[C:4]([CH:6]1[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:9]1)(=[O:5])[CH3:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylateHCID 178420676HCID 178420676, compound

Product 1

HCID 59841137tert-Butyl 3-acetylazetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 ml round bottom flask was added tert-butyl 3-{[methoxy(methyl)amino]carbonyl}azetidine-1-carboxylate (2.6 g, 10.6 mmol) and 20 ml tetrahydrofuran. The resulting solution was cooled to 0° C. and methylmagnesium chloride tetrahydrofuran solution (4.3 ml, 3M, 12.8 mmol) was added by a syringe. The reaction mixture was stirred at 0° C. for 1 hour. It was diluted with 100 ml ether, and the resulting mixture was washed twice with 100 ml saturated ammonium chloride solution. The organics were dried over sodium sulfate, filtered and concentrated. The crude product was used for the next step without further purification.

Workup

  1. washthe resulting mixture was washed twice with 100 ml saturated ammonium chloride solution
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-014304f82c5a4e3ab0a999318d9b16f4
Source dataset
uspto-grants-2012_11
Patent number
US08304434B2

Reaction notes

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