Pyridine → 2(R)-acetoxycyclopent-1(R)-yl chloroformate
Reaction equation
[CH3:1][C:2]([O:4][C@H:5]1[C@H:9]([OH:10])[CH2:8][CH2:7][CH2:6]1)=[O:3].N1C=CC=CC=1.[Cl:17][C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[Cl:17][C:18]([O:10][C@@H:9]1[CH2:8][CH2:7][CH2:6][C@H:5]1[O:4][C:2](=[O:3])[CH3:1])=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of (1R,2R)-trans-2-acetoxy-1-cyclopentanol (1.0 g, 6.9 mmol) in dichloromethane (25 mL) at 0° C. under nitrogen atmosphere was added pyridine (0.88 mL, 10.4 mmol) followed by a solution of triphosgene (1.03 g, 3.5 mmol) in dichloromethane (25 mL). The reaction mixture was stirred at 0° C. for 30 min. to provide the corresponding 2(R)-acetoxycyclopent-1(R)-yl chloroformate which was carried to next step without further purification.
Sources & evidence
- ORD record
- ord-53422130f6eb46a581f63f2b6cc77946
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026351B2
Reaction notes
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