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

HRID 2276386노트

반응식

HRID 2276386 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

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]+).

후처리

  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

출처 및 근거

ORD 기록
ord-dfd07dfc2cdf49e3b2f364273de3a176
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09132136B2

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