1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate

HRID 338938노트

반응식

HRID 338938 반응식
[OH:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Cl[C:16]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:1][C@@H:2]2[C@@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)=[CH:30][CH:29]=1

참가 물질

4

반응물 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 13329885tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate

생성물 1

HCID 86707461(3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate수율 65%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of (3S,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate (2.79 g, 13.7 mmol) in anhydrous pyridine (144 mL) was added 4,4′-(chloro(phenyl)methylene)bis(methoxybenzene) (5.43 g 15.2 mmol) and the resulting mixture stirred at ambient temperature for 4 days. The reaction was quenched with methanol (10 mL) and concentrated under reduced pressure. The residue was stirred in diethyl ether (150 mL) and the solid which precipitated was collected by filtration. The filtrate was concentrated under reduced pressure and purified by column chromatography (Biotage, 40M; 1% methanol:dichloromethane) to afford (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate (4.48 g, 65%).

후처리

  1. customThe reaction was quenched with methanol (10 mL)
  2. concentrationconcentrated under reduced pressure
  3. stirringThe residue was stirred in diethyl ether (150 mL)
  4. customthe solid which precipitated
  5. filtrationwas collected by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography (Biotage, 40M; 1% methanol:dichloromethane)

출처 및 근거

ORD 기록
ord-37b5001076fa4bceb9a55543c9b63e49
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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