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

HRID 338938ノート

反応式

HRID 338938 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-37b5001076fa4bceb9a55543c9b63e49
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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