HCID 66670645、化合物 → tert-Butyl trans-3-Hydroxy-4-phenylpyrrolidine-1-carboxylate

HRID 1896210ノート

反応式

HRID 1896210 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([CH2:11]2)[O:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC1CCCO1.[Cu](I)I>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:10]([OH:9])[CH2:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 2

HCID 66670645HCID 66670645、化合物HCID 178418255HCID 178418255、化合物

生成物 1

HCID 73553444tert-Butyl trans-3-Hydroxy-4-phenylpyrrolidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 73012-Methyltetrahydrofuran溶媒

実験手順

Oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (3 g, 16 mmol), was dissolved in 2-methyl-tetrahydrofuran (5 mL) and added dropwise to a solution of phenylmagnesium bromide (1.5 eq, 24.3 mL of a 1.0 M solution) and copper iodide (0.05 eq) at 0° C. The reaction was allowed to warm to room temperature and stir for 18 h. Reaction was cooled to 0° C. and quenched with sat. NH4Cl solution and extracted with EtOAc. Organic was washed with NaHCO3 and brine and dried over Na2SO4 and the solvent removed. Residue was purified by column chromatography on SiO2 (15-40% EtOAc/HEptane) which gave the title compound Ia as a yellow oil (3.59 g).

後処理

  1. customReaction
  2. temperaturewas cooled to 0° C.
  3. customquenched with sat. NH4Cl solution
  4. extractionextracted with EtOAc
  5. washOrganic was washed with NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed
  8. customResidue was purified by column chromatography on SiO2 (15-40% EtOAc/HEptane) which

出典と根拠

ORDレコード
ord-9e54190928a24422ad5990a5ef525f6a
出典データセット
uspto-grants-2013_08
特許番号
US08518952B2

反応ノート

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