Toluene → 4(S)-t-Butyloxycarbonylamino-5-cyclohexyl-3(R,S)hydroxy-1-pentene
反応式
C[O:2][C:3](=O)[C@H:4](C)[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1CCCCC1.[H-].C([Al+]CC(C)C)C(C)C.[CH:31]([Mg]Br)=[CH2:32].[C:35]1([CH3:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[C:15]([O:14][C:12]([NH:5][C@@H:4]([CH2:41][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[CH:3]([OH:2])[CH:31]=[CH2:32])=[O:13])([CH3:18])([CH3:17])[CH3:16]参加物
反応条件
- 温度
- 0 °C
実験手順
To a stirred -78° C. solution of Boc-cyclohexylalanine methyl ester (10.2 g, 35.8 mmol) in dry toluene (60 mL) was added diisobutylaluminum hydride (34 mL of a 1.5M solution in toluene) After 30 minutes, vinyl magnesium bromide (108 mL of 1M solution in THF) was added. After stirring for 15 hours at 0° C., the mixture was carefully quenched with methanol, treated with Rochelle salts (22 mL of saturated aqueous solution in 140 mL H2O), and filtered. After extracting the solids 5 times with ethyl acetate, the extracts and filtrate were combined and the organic phase was washed with brine, dried, filtered, and evaporated to an oil (10.2 g). Chromatography on silica gel eluting with hexane/ethyl acetate mixtures provided 6.1 g (60%) of the desired product.
後処理
- customthe mixture was carefully quenched with methanol
- additiontreated with Rochelle salts (22 mL of saturated aqueous solution in 140 mL H2O)
- filtrationfiltered
- extractionAfter extracting the solids 5 times with ethyl acetate
- washthe organic phase was washed with brine
- customdried
- filtrationfiltered
- customevaporated to an oil (10.2 g)
出典と根拠
- ORDレコード
- ord-a73436c03f90465685acfe264731bff4
- 出典データセット
- uspto-grants-1993_05
- 特許番号
- US05214129
反応ノート
読み込み中…