반응식
C[O:2][C:3]([C:5]1([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.[BH4-].[Li+]>C1COCC1>[OH:2][CH2:3][C:5]1([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:9][CH2:10]1참가 물질
실험 절차
The crude tert-butyl 4-methoxycarbonyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (assumed 44 mmol) from Step A was taken up in THF (200 mL) and 2M lithium borohydride in THF (29 mL, 58 mmol) was added via syringe at room temperature. The reaction was stirred for 2 days at room temperature and then at 50° C. for 20 h after addition of more 2M lithium borohydride in THF (2.9 mL, 5.8 mmol). The mixture was then quenched with acetic acid, diluted with ether and aq. sodium bicarbonate solution, and extracted three times with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (20% ethyl acetate in hexanes) to afford recovered starting material (2.5 g) and the title product (7.1 g).
후처리
- customThe mixture was then quenched with acetic acid
- additiondiluted with ether and aq. sodium bicarbonate solution
- extractionextracted three times with ether
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (20% ethyl acetate in hexanes)
- customto afford
- customrecovered
출처 및 근거
- ORD 기록
- ord-0677070e85e2467c947e5de20344088b
- 출처 데이터셋
- uspto-grants-2006_08
- 특허 번호
- US07091211B2
연결된 노트
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