Isopropanol → (S)-2-amino-1-(3-chlorophenyl)ethanol
反応式
[N:1]([CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[OH:6])=[N+]=[N-].[BH4-].[Na+].C(O)(C)C>CO>[NH2:1][CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[OH:6]参加物
5
反応条件
- 温度
- 80 °C
実験手順
A mixture of (S)-2-Azido-1-(3-chlorophenyl)-ethanol (5.14 g, 0.026 mol), NaBH4 (1.97 g, 0.052 mol) and isopropyl alcohol (100 mL) was stirred at 80° C. for 24 h. The solvent was evaporated, the residue was separated on SiO2 (15 g) CHCl3-MeOH (0 to 30%). Colorless oil, 3.70 g (0.021 mol, 83%). The material was reacted with Boc2O in dichloromethane and NEt3 and analyzed by chiral SFC using a CHIRALPAK AD-H column, 30% MeOH and determined to be 91% ee. LCMS [M+H]+ 172.4
後処理
- customThe solvent was evaporated
- customthe residue was separated on SiO2 (15 g) CHCl3-MeOH (0 to 30%)
- customThe material was reacted with Boc2O in dichloromethane and NEt3
出典と根拠
- ORDレコード
- ord-978cb1748d4c411b8b6a61bdaa139fa7
- 出典データセット
- uspto-grants-2014_04
- 特許番号
- US08686005B2
反応ノート
読み込み中…