Tert-butyl 3-oxopyrrolidine-1-carboxylate → tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate

HRID 1373152노트

반응식

HRID 1373152 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][Mg]Br>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([OH:13])([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418573HCID 178418573, 화합물2회

생성물 1

HCID 22951485tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate수율 37%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

3-Oxo-pyrrolidine-1-carboxylic acid tert-butyl ester [Hofmann, J. Agric. Food Chem., 46, 3902 (1998)] (0.322 g, 1.74 mmol) was dissolved in diethyl ether (5 ml), cooled with an ice bath, and treated with methylmagnesium bromide (3M in ether, 0.64 ml, 1.91 mmol). The reaction was stirred for 1 h then more methylmagnesium bromide added, and the mixture stirred for 63 h. The reaction was quenched with aqueous ammonium chloride and extracted with diethyl ether (×3). The combined organic extracts were dried and evaporated. The residue was purified by flash chromatography, eluting with 0–50% ethyl acetate in petroleum ether, to give the title compound as a sticky off-white solid (0.129 g, 37%); NMR (CDCl3) 1.41 (3H, s), 1.46 (9H, s), 1.61 (1H, s), 1.79–1.92 (2H, m), and 3.17–3.58 (4H, m).

후처리

  1. temperaturecooled with an ice bath
  2. stirringthe mixture stirred for 63 h
  3. customThe reaction was quenched with aqueous ammonium chloride
  4. extractionextracted with diethyl ether (×3)
  5. customThe combined organic extracts were dried
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 0–50% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-632aa4c569c740289caf197d8ee4d6eb
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160907B2

반응 노트

불러오는 중…