Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Azetidine | HCID 10422 | — |
| Reactant | Phenyl chloroformate | HCID 15891 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 12025112 | HCID 12025112 | 72.4% |
Reaction Steps
To a stirred solution of azetidine (2 g, 35.08 mmol) in DCM (25 mL) were added triethylamine (14.4 mL, 105.24 mmol), followed by phenyl chloroformate (5.5 mL, 42.10 mmol) at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 16 h. Then the reaction mixture was diluted with water (30 mL) and extracted with DCM (2×50 mL). The organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue which was purified by column chromatography using mixture of 5% MeOH/DCM as an eluent to get the desired compound as a white solid (4.5 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ 7.39-7.35 (m, 2H), 7.22-7.18 (m, 1H), 7.12-7.08 (m, 2H), 4.20-4.08 (m, 2H), 4.04-3.92 (m, 2H), 2.29-2.21 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09062075B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-f8fe6e8ef73d4e32b1b5e64ccc7f1182 |
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| Source note | uspto-grants-2015_06 |
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