Triethylamine → 4-Benzyl-1,3-oxazolidin-2-one
Reaction equation
CCN(CC)CC.CC(C)(C)C(Cl)=O.[CH2:15]([C@H:22]1[CH2:26][O:25][C:24](=[O:27])[NH:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Li].C([O-])(O)=O.[Na+]>CCOC(C)=O.C1COCC1>[CH2:15]([CH:22]1[CH2:26][O:25][C:24](=[O:27])[NH:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 13-5 (5.6 g, 19 mmol), THF (97 mL), and NEt3 (3.2 mL, 23 mmol) at −78° C. was added trimethylacetyl chloride (2.6 mL, 21 mmol) dropwise. After addition was complete, the reaction mixture was warmed to 0° C. for 2 h then recooled to −78° C. and treated with lithium (S)-(−)-4-benzyl-2-oxazolidinone (18 mL, 29 mmol; 1.6M solution in THF). The reaction mixture was then warmed to 0° C. for 1 h and poured into EtOAc (300 mL) and sat. NaHCO3 (30 mL). The organic phase was washed with sat. NaHCO3, H2O, and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, EtOAc) gave 13-6 as an oil.
Workup
- additionAfter addition
- customthen recooled to −78° C.
- temperatureThe reaction mixture was then warmed to 0° C. for 1 h
- washThe organic phase was washed with sat. NaHCO3, H2O, and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6d03cdabb25340e683ac47d6328de448
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297249B1
Reaction notes
Loading…