HCID 66670645, 화합물 → tert-Butyl trans-3-Hydroxy-4-phenylpyrrolidine-1-carboxylate

HRID 1896210노트

반응식

HRID 1896210 반응식
[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]

참가 물질

5

반응물 2

HCID 66670645HCID 66670645, 화합물HCID 178418255HCID 178418255, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 73012-Methyltetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9e54190928a24422ad5990a5ef525f6a
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518952B2

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