Dimethyl Sulfoxide → HCID 18782626, compound
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([CH2:17][O:18][C:19]([N:21]2[CH2:26][CH2:25][CH2:24][C@@H:23]([OH:27])[C@H:22]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([CH2:17][O:18][C:19]([N:21]2[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH:22]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:20])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -75 °C
Procedure
Dimethyl sulfoxide (9.1 mL, 10.0 g, 128.6 mmol) in dichloromethane (50 mL) was added slowly to a cooled (-75° C.) solution of oxalyl chloride (6.9 mL, 10.2 g, 80.4 mmol) in dichloromethane (500 mL). The mixture was stirred at -75° C. for 15 min., then (2R,3R)-1-(phenylmethoxycarbonyl)-2-phenylpiperidin-3-ol (Description 79, 20.0 g, 64.3 mmol) was added slowly. The mixture was stirred at -75° C. for 1 h., then triethylamine (27 mL, 19.5 g, 192.9 mmol) was added. The mixture was stirred at -75° C. for 1 h., then at room temperature overnight. The mixture was washed with aqueous citric acid (1M), aqueous sodium hydrogen carbonate, water, and brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a yellow oil (19.56 g, 98%). 1H NMR (250 MHz, CDCl3) δ7.39-7.20 (10 H, m), 5.74 (1 H, br s), 5.17 (2 H, br s), 4.13 (1 H, br s), 3.40 (1 H, br m), 2.47 (2 H, m), and 1.94 (2 H, m).
Workup
- stirringThe mixture was stirred at -75° C. for 1 h.
- stirringThe mixture was stirred at -75° C. for 1 h.
- customat room temperature
- customovernight
- washThe mixture was washed with aqueous citric acid (1M), aqueous sodium hydrogen carbonate, water, and brine
- dry with materialdried (MgSO4)
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1ecd072b173249c7bda994a09f85e5b3
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06071927
Reaction notes
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