Aluminium lithium hydride → (1-Benzyl-4-(4-chlorophenyl)-3-methylpyrrolidin-3-YL)methanol

HRID 1891321노트

반응식

HRID 1891321 반응식
C([O:3][C:4]([C:6]1([CH3:25])[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:9][N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:18]([N:8]1[CH2:9][CH:10]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[C:6]([CH2:4][OH:3])([CH3:25])[CH2:7]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 66653488HCID 66653488, 화합물

생성물 1

HCID 66653293(1-Benzyl-4-(4-chlorophenyl)-3-methylpyrrolidin-3-YL)methanol수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (3RS,4RS)-1-benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidine-3-carboxylic acid ethyl ester (5.75 g, 16.7 mmol) in THF (200 mL) at 0° C., was added portion wise LiAlH4 (381 mg, 10.0 mmol) over 20 minutes. After one hour at this temperature, the reaction mixture was carefully quenched by addition of icy water and then of an aqueous solution of NaHCO3. The product was extracted with EtOAc several times, the combined organic phases were dried over NA2SO4 and purification by column chromatography (SiO2, EtOAc/H 1:4 to 1:1) yielded the title product (4.0 g, 76%) as a colorless viscous oil. ES-MS m/e: 316.2 (M+H+).

후처리

  1. customthe reaction mixture was carefully quenched by addition of icy water
  2. extractionThe product was extracted with EtOAc several times
  3. dry with materialthe combined organic phases were dried over NA2SO4 and purification by column chromatography (SiO2, EtOAc/H 1:4 to 1:1)

출처 및 근거

ORD 기록
ord-33bc395525f94673a4c5ad776ea16a7b
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507535B2

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