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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
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HRID 906941 반응식
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]
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-962ccf39dbc94bfa9b2b2598a1f64144
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012998B2

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