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Water → [(3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methanol

HRID 1880227
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HRID 1880227 반응식
C[O:2][C:3]([C@@H:5]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:8][N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:18]([N:7]1[CH2:8][C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[C@@H:5]([CH2:3][OH:2])[CH2:6]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
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참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67232866methyl (3R*,4S*)-1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

생성물 1

HCID 67533568[(3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methanol

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

(3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (28.5 g, 0.078 mol) were dissolved in THF (800 mL). At 0° C. LiAlH4 (3.12 g, 0.082 mol) was added portion wise. After stirring at 0° C. for 4 h water (20 mL), then 5N NaOH (20 mL) and additional water (30 mL) was added. After stirring at ambient temperature for 30 min the mixture was extracted with ethyl acetate (3×10 mL), the combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude title product was obtained as a white solid (25.0 g, 95%) and directly used in the next step. ES-MS m/e: 337.8 (M+H+).

후처리

  1. customAt 0° C
  2. extractionwas extracted with ethyl acetate (3×10 mL)
  3. customthe combined organic phases were dried on sodium sulfate
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-6bf932779b4c436b9ceedb306ad57c81
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318759B2

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