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Trimethylsilyldiazomethane → Methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoate

HRID 8747
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HRID 8747 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])([C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

4

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 219839874-(1-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoic acid

생성물 1

HCID 69183850Methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoate수율 82.4%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution of 4-(1-(tert-butoxycarbonyl)-4-(methoxy-carbonyl)piperidin-4-yl)butanoic acid (23.4 g, 0.071 mol) from Step D in 3:1 dichloromethane/methanol (480 mL) at 0° C. was added a solution of trimethylsilyldiazomethane (53 mL, 0.11 mol, 2.0M in hexane). The reaction mixture was stirred for 15 min and then concentrated to afford 25.5 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (20.1 g).

후처리

  1. concentrationconcentrated
  2. customto afford 25.5 g
  3. customThe residue was purified by flash chromatography
  4. washeluting with 20–30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-6b2aefe82fc74fb8a87e403b637a98cc
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07091211B2

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