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Methanamine, N-methoxy-, hydrochloride (1:1) → (3R,4S)-1-Benzyl-4-(3,4-difluoro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide

HRID 906941
ノート
印刷プレビュー

反応式

HRID 906941 の反応式
Cl.CN[O:4][CH3:5].C[Al](C)C.C([C@H:17]1COC(=O)[N:18]1[C:23]([C@@H:25]1[C@@H:29]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=2)[CH2:28][N:27]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:26]1)=[O:24])C1C=CC=CC=1>C(Cl)Cl>[CH3:5][O:4][N:18]([CH3:17])[C:23]([C@@H:25]1[C@@H:29]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=2)[CH2:28][N:27]([CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:26]1)=[O:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 16682925TrimethylaluminumHCID 67131567(S)-4-benzyl-3-[(3R,4S)-1-benzyl-4-(3,4-difluoro-phenyl)-pyrrolidine-3-carbonyl]-oxazolidin-2-one

生成物 1

HCID 86627624(3R,4S)-1-Benzyl-4-(3,4-difluoro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide収率 90%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

To a suspension of N,O-dimethylhydroxylamine hydrochloride (7.82 g, 80.6 mmol) in DCM (130 mL) at RT was added trimethylaluminium (2.0M solution in heptane, 40.3 ml, 80.6 mmol) dropwise and stirring was continued for one hour. To this mixture was added a solution of (S)-4-benzyl-3-[(3R,4S)-1-benzyl-4-(3,4-difluoro-phenyl)-pyrrolidine-3-carbonyl]-oxazolidin-2-one (19.2 g, 40.3 mmol) in DCM (100 mL) over 10 minutes. Stirring was continued for three hours. The reaction was quenched by an addition of aq. Potassium sodium tartarate solution and extracted with ethyl acetate. The separated organic layer was washed with brine and dried on Na2SO4 and concentrated under vacuo. Its purification by column chromatography (SiO2, EtOAc/H, 15:85) yielded 13 g (90%) of the title compound as a light yellow oil. ES-MS m/e: 361.2 (M+H+).

後処理

  1. stirringStirring
  2. waitwas continued for three hours
  3. customThe reaction was quenched by an addition of aq. Potassium sodium tartarate solution
  4. extractionextracted with ethyl acetate
  5. washThe separated organic layer was washed with brine
  6. customdried on Na2SO4
  7. concentrationconcentrated under vacuo
  8. customIts purification by column chromatography (SiO2, EtOAc/H, 15:85)

出典と根拠

ORDレコード
ord-962ccf39dbc94bfa9b2b2598a1f64144
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08012998B2

反応ノート

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