Tetrahydrofuran → HCID 70014061, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:10][C@@H:9]1[C@H:11]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:12][Cl:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([Mg]Cl)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1COCC1.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[Si:15]([O:14][C@@H:11]([C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:10][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:12][Cl:13])([C:18]([CH3:21])([CH3:19])[CH3:20])([CH3:16])[CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a magnetically stirred solution of N-t-butyloxycarbonyl-2(R)-(1(S)-t-butyldimetylsilyloxy-2-chloroethyl)aziridine (36.0 mg, 0.107 mmol) in toluene was added copper bromide dimethyl sulfide complex (11.0 mg, 0.054 mmol) at rt under N2. The reaction mixture was cooled to −78° C. then treated with a 2 M solution of PhMgCl in THF (0.54 mL, 1.072 mmol). The resulting mixture was warmed to −20° C. and stirred overnight. The reaction mixture was treated with sat NH4Cl (4 mL) and extracted with EtOAc(5 mL×3). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated and column-chromatographed (3% EtAc in n-Hex) to provide 2(S)-t-butyldimetylsilyloxy-3(R)-(t-butyloxycarbonyl)amino-1-chloro-4-phenylbutane (33.5 mg) as a colorless oil.
Workup
- temperatureThe resulting mixture was warmed to −20° C.
- extractionextracted with EtOAc(5 mL×3)
- washThe combined organic layers were washed with brine (50 mL)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customcolumn-chromatographed (3% EtAc in n-Hex)
Sources & evidence
- ORD record
- ord-13f4235db4994afbb606a13c157d7c0e
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06573388B1
Reaction notes
Loading…