Hydrochloric Acid → 3-(4-Tert-butoxycarbonylaminophenyl)propanol

HRID 1978392ノート

反応式

HRID 1978392 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](OCC)=[O:28])=[CH:21][CH:20]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21994026Ethyl 3-(4-tert-butoxycarbonylaminophenyl)propionate

生成物 1

HCID 219940133-(4-Tert-butoxycarbonylaminophenyl)propanol収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Diisobutylaluminium hydride(l.5 M in toluene, 30.5 ml, 45.8 mmol) was added dropwise to a stirred solution of ethyl 3-(4-tert-butoxycarbonylaminophenyl)propionate (6.10 g, 20.8 mmol) in tetrahydrofuran (60 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hour. 2N-hydrochloric acid was added to the mixture and the mixture was extracted with ethyl acetate. The extract was successively washed with water, saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2) to give 3-(4-tert-butoxycarbonylaminophenyl)propanol as a colorless oil (2.66 g, 51%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was successively washed with water, saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2)

出典と根拠

ORDレコード
ord-2707dce753ee478ba7fbac6412c6619f
出典データセット
uspto-grants-2001_05
特許番号
US06235731B1

反応ノート

読み込み中…