Ammonium formate → (S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate

HRID 2276386ノート

反応式

HRID 2276386 の反応式
C1(C(=[N:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)=[CH:17][CH:16]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 86654632(S)-tert-butyl 2-(4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate

生成物 1

HCID 66705988(S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate収率 94%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

A suspension of (S)-tert-Butyl 2-(4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate (54.1 g), ammonium formate (116 g) and 5% palladium on charcoal (6.5 g) in methanol (930 ml) was stirred at 60° C. for 2 h. The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate and water. The organic phase was extracted twice with 0.5 M aq. HCl. The combined aqueous phases were basified with 2 M aq. NaOH and extracted twice with dichloromethane. The organic phases were dried over magnesium sulfate, filtered and dried in vacuo to yield (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (31.95 g, 94%) as an off-white solid. MS (ISP): 279.1 ([M+H]+).

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionThe organic phase was extracted twice with 0.5 M aq. HCl
  5. extractionextracted twice with dichloromethane
  6. dry with materialThe organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-dfd07dfc2cdf49e3b2f364273de3a176
出典データセット
uspto-grants-2015_09
特許番号
US09132136B2

反応ノート

読み込み中…