Triethylamine → Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate
Reaction equation
[OH:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].[Cl-].[NH4+]>C(Cl)Cl.O>[CH3:21][S:22]([O:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1)(=[O:24])=[O:23]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (8.8 g, 47 mmol) in DCM (188 mL) at 0° C., triethylamine (7.8 mL, 56 mmol) was added in one portion. Then, neat methanesulfonyl chloride (4.38 mL, 56 mmol) was added via an additional funnel over 30 minutes. The resulting mixture was stirred at 0° C. for 1.5 h. Upon completion of the reaction, water (100 mL) and sat'd aqueous ammonium chloride (100 mL) were added respectively. The organic phase was separated and washed twice with water, washed with brine, dried over Na2SO4, filtered, and concentrated to afford the crude tert-butyl 3-(((methylsulfonyl)oxy)methyl)azetidine-1-carboxylate as a pale yellow oil (12.5 g). This compound was used directly for the next step without further purification.
Workup
- additionwere added respectively
- customThe organic phase was separated
- washwashed twice with water
- washwashed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-642c2fe3f269448185c4b2f7f08763b8
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193714B2
Reaction notes
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