2-Butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester → HCID 66687362、化合物

HRID 661539ノート

反応式

HRID 661539 の反応式
[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]

参加物

4

反応物 2

HCID 866208582-Butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178478192HCID 178478192、化合物

生成物 1

HCID 66687362HCID 66687362、化合物収率 46%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-bc49f4b6a00e49a98515db3a6aabd6c5
出典データセット
uspto-grants-2011_12
特許番号
US08084623B2

反応ノート

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