HCID 86620858, 화합물 → HCID 66687362, 화합물

HRID 661539

반응식

HRID 661539 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:15][CH2:16][CH2:17][CH3:18])[CH:13]=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:19][C:20]1[CH:21]=[C:22]([Mg]Br)[CH:23]=[CH:24][C:25]=1[Cl:26]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:15][CH2:16][CH2:17][CH3:18])[CH:13]([C:23]1[CH:22]=[CH:21][C:20]([Cl:19])=[C:25]([Cl:26])[CH:24]=1)[OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 86620858HCID 86620858, 화합물HCID 178478192HCID 178478192, 화합물

생성물 1

HCID 66687362HCID 66687362, 화합물수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 2-butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.753 g, 2.95 mmol) in THF (12 mL) at 0° C. and under nitrogen was added 3,4-dichlorophenylmagnesium bromide (11.8 mL of a 0.5 M solution in pentanes, 5.9 mmol) dropwise over 10 minutes. After 20 minutes, the reaction mixture was quenched by the addition of saturated aqueous NH4Cl (30 mL) then extracted with EtOAc. The combined extracts were washed with brine then dried (MgSO4), filtered and concentrated in vacuo to a yellow oil (1.9 g). Purification by chromatography (silica, 5-20% EtOAc in hexanes) gave 2-butyl-2-[(3,4-dichloro-phenyl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.548 g, 1.36 mmol, 46%) as a colourless gum and as an inseparable mixture of diastereomers

후처리

  1. customthe reaction mixture was quenched by the addition of saturated aqueous NH4Cl (30 mL)
  2. extractionthen extracted with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a yellow oil (1.9 g)
  7. customPurification by chromatography (silica, 5-20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-bc49f4b6a00e49a98515db3a6aabd6c5
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084623B2

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