반응식
[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:31]CC1.[OH-].[Na+].OO.Cl>C1COCC1.O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@@:4]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)([CH2:1][CH2:2][CH2:3][OH:31])[O:9][C:8]2=[O:10])[CH3:12])=[CH:14][CH:15]=1참가 물질
반응물 5
생성물 1
시약·촉매·용매 2
실험 절차
To a solution of (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (1 g, 2.4 mmol) in dry THF (15 mL) was added dropwise BH3.THF (5 mL, 1 M) at 0° C. After stirring for 2 h at rt, the reaction mixture was cooled to 0° C. and water (1 mL), aqueous NaOH (0.5 mL, 3 M) and H2O2 (0.5 mL, 30%) were successively added. The mixture was stirred for 2-3 h at rt and diluted with water (8 mL). The pH was adjusted to 6-7 with 0.5 N HCl. The layers were separated, and the aqueous phase was extracted with EtOAc (3×10 mL). The combined organic layers were washed with a satd aq NaHCO3 (20 mL) and brine (20 mL), dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified by preparative TLC to afford (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (400 mg, 38%).
후처리
- temperaturethe reaction mixture was cooled to 0° C.
- stirringThe mixture was stirred for 2-3 h at rt
- customThe layers were separated
- extractionthe aqueous phase was extracted with EtOAc (3×10 mL)
- washThe combined organic layers were washed with a satd aq NaHCO3 (20 mL) and brine (20 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customto give the crude product, which
- customwas purified by preparative TLC
출처 및 근거
- ORD 기록
- ord-777d15558a884a608f6e33241bcbaa67
- 출처 데이터셋
- uspto-grants-2013_07
- 특허 번호
- US08487094B2
연결된 노트
불러오는 중…