Boron Trichloride → HCID 10383657, compound
Reaction equation
C([O:8][CH2:9][C@:10]1([CH2:16][O:17][C:18](=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[O:14][C:13](=[O:15])[CH2:12][CH2:11]1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[C:18]([O:17][CH2:16][C@@:10]1([CH2:9][OH:8])[O:14][C:13](=[O:15])[CH2:12][CH2:11]1)(=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.15 (0.036 g, 0.08 mmol) in CH2Cl2 (4 mL) was cooled to -78° C., treated with boron trichloride (1.0M in dichloromethane, 0.24 mL, 0.24 mmol), and stirred at that temperature for 1.5 h. The reaction mixture was quenched by the slow addition of a saturated NaHCO3 solution (0.3 mL) at -78° C., and immediately partitioned between ice-cold ether and a pH 7 buffer solution. The organic layer was washed five times with the pH 7 buffer solution, dried (Na2SO4), and concentrated to give a white solid. This solid was washed with cold hexane several times to give a pure sample of 2.2 (24 mg, 84%) as a solid; mp 65°-66° C.; [α]22D +1.43° (c 4.2, CHCl3). The IR, 1H NMR, and 13C NMR were identical to those reported for the racemate (3e, Example 1).
Workup
- customThe reaction mixture was quenched by the slow addition of a saturated NaHCO3 solution (0.3 mL) at -78° C.
- customimmediately partitioned between ice-cold ether
- washThe organic layer was washed five times with the pH 7 buffer solution
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customto give a white solid
- washThis solid was washed with cold hexane several times
Sources & evidence
- ORD record
- ord-425a825f45d84b7790e9da61f69804d0
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05874464
Reaction notes
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