1-Chloroethyl chloroformate → 3-((Tert-butyldiphenylsilyl)oxy)azetidine
Reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCCl>[C:32]([Si:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[O:18][CH:16]1[CH2:15][NH:14][CH2:17]1)([CH3:35])([CH3:33])[CH3:34]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A stirred solution of 1-benzhydryl-3-(tert-butyl-diphenyl-silanyloxy)-azetidine (162a) (4.0 g, 8.4 mmol) in DCE (60 ml) at room temperature is treated with 1-chloroethylchloroformate (1.2 ml, 10.9 mmol) and the reaction mixture is heated to 80° C. After 2 hours, the solvent is removed in vacuo and the residue is dissolved in methanol (60 ml) and heated to reflux. After 1 h the reaction mixture is poured into water (250 ml), acidified with hydrochloric acid (1M solution) and washed with EtOAc (3×75 ml). The aqueous solution is basified with saturated sodium bicarbonate solution and extracted with EtOAc (3×75 ml). The combined organic layers are washed with water (2×50 ml), brine (50 ml), dried over MgSO4. The solvent is removed in vacuo to yield the titled compound.
Workup
- customthe solvent is removed in vacuo
- dissolutionthe residue is dissolved in methanol (60 ml)
- temperatureheated to reflux
- additionAfter 1 h the reaction mixture is poured into water (250 ml)
- washwashed with EtOAc (3×75 ml)
- extractionextracted with EtOAc (3×75 ml)
- washThe combined organic layers are washed with water (2×50 ml), brine (50 ml)
- dry with materialdried over MgSO4
- customThe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-c95ae3b4b4b54f868d3c8741123dcc10
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129541B2
Reaction notes
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