Hydroxyamine hydrochloride → (R)-tert-butyl 2-(4-amino-2-fluorophenyl)morpholine-4-carboxylate

HRID 2403333노트

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HRID 2403333 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)=[C:17]([F:34])[CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO>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]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:22]2)=[C:17]([F:34])[CH:16]=1

참가 물질

5

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86671413(R)-tert-butyl 2-(4-(diphenylmethyleneamino)-2-fluorophenyl)morpholine-4-carboxylate

생성물 1

HCID 68325616(R)-tert-butyl 2-(4-amino-2-fluorophenyl)morpholine-4-carboxylate수율 85%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

To a stirred solution of (R)-tert-butyl 2-(4-(diphenylmethyleneamino)-2-fluorophenyl)morpholine-4-carboxylate (5.95 g) in methanol (50 ml) were added sodium acetate (2.93 g) and hydroxylamine hydrochloride (1.82 g). The reaction mixture was stirred at 50° C. overnight. The reaction mixture was then filtered through sintered glass and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in hexanes) to afford (R)-tert-butyl 2-(4-amino-2-fluorophenyl)morpholine-4-carboxylate (3.0 g, 85%) as a yellow solid. MS (ISP): 296 ([M]+), 240 ([M-C4H8]+), 195 ([M+H—C4H8—CO2H]+).

후처리

  1. filtrationThe reaction mixture was then filtered through sintered glass
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-01db3347afd7432ca5c5909882a549b5
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802673B2

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