Water → 1-Tert-butyloxycarbonyl-cis-2-formyl-5-phenylpyrrolidine

HRID 1162829노트

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HRID 1162829 반응식
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@@H:9]1[C:19](N(OC)C)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].S(=O)(=O)(O)[O-].[K+].O>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10][C@@H:9]1[CH:19]=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 866174771-Tert-butyloxycarbonyl-cis-2-{[methoxy(methyl)amino]carbonyl}-5-phenylpyrrolidine

생성물 1

HCID 541676581-Tert-butyloxycarbonyl-cis-2-formyl-5-phenylpyrrolidine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a cold (−78° C.) solution of 1-tert-butyloxycarbonyl-cis-2-{[methoxy(methyl)amino]carbonyl}-5-phenylpyrrolidine (1.36 g, 4.07 mmol) in THF (20 mL) under an atmosphere of nitrogen, a 1M solution of LAH in THF (4.07 mL, 4.07 mmol) was added dropwise and the mixture was stirred for 30 min. The mixture was warmed to 0° C. for 30 min and then quenched with potassium bisulfate solution in water (0.969 g, 7.12 mmol). EtOAc was added and the organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 50:50 mixture of ethyl acetate and hexane. Collection and concentration of appropriate fractions provided 1-tert-butyloxycarbonyl-cis-2-formyl-5-phenylpyrrolidine. HPLC RT=3.47 min, 99% at 215 nm (Method A); ES MS (M+H)=276.3.

후처리

  1. customthe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. additionThe residue was subjected to column chromatography on silica gel eluting with a 50:50 mixture of ethyl acetate and hexane
  7. customCollection and concentration of appropriate fractions

출처 및 근거

ORD 기록
ord-ee4ff0ff38904d3f83c0e766d51ee13b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820680B2

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