2-Methyltetrahydrofuran → tert-Butyl 1-(3-methyl-1,2,4-oxadiazole-yl)-3-azabicyclo[3.1.0]hexan-3-carboxylate

HRID 1477503노트

반응식

HRID 1477503 반응식
CC1CCCO1.[C:7](=[N:10][OH:11])([NH2:9])[CH3:8].C[O-].[Na+].[C:15]12([C:28](OCC)=O)[CH2:20][CH:19]1[CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]2>O>[CH3:8][C:7]1[N:9]=[C:28]([C:15]23[CH2:20][CH:19]2[CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]3)[O:11][N:10]=1

참가 물질

6

반응물 4

HCID 73012-MethyltetrahydrofuranHCID 30926N-HydroxyacetamidineHCID 10942334Sodium MethoxideHCID 53249947Ethyl 3-Boc-3-azabicyclo[3.1.0]hexane-1-carboxylate

생성물 1

HCID 58487578tert-Butyl 1-(3-methyl-1,2,4-oxadiazole-yl)-3-azabicyclo[3.1.0]hexan-3-carboxylate수율 53.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2-Methyltetrahydrofuran (15 mL), acetamide oxime (2.54 g, 34.3 mmol) and sodium methoxide (3.70 g, 68.6 mmol) were added to 3-tert-butyl 1-ethyl 3-azabicyclo[3.1.0]hexane-1,3-dicarboxylate (103) (3.5 g, 13.72 mmol) and the mixture was heated to reflux for 20 minutes. Upon cooling the suspension was treated with 60 mL of water and extracted with ethyl acetate (2×50 mL). The combined organics were washed with saturated sodium chloride and dried over magnesium sulfate. The mixture was concentrated and the residue was chromatographed over 20 g of silica gel with hexanes/ethyl acetate; obtained 1.95 g of 104 as a white solid. MS (ESI) m/z 304.0 [M+K]+. 1H NMR (CDCl3) δ: 1.17 (m, 1H), 1.46 (s, 9H), 1.74 (m, 1H), 2.18 (s, 2H), 2.22 (m, 1H), 2.36 (s, 3H), 3.50 (m, 1H), 3.70 (m, 1H).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 minutes
  3. temperatureUpon cooling the suspension
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organics were washed with saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe mixture was concentrated
  8. customthe residue was chromatographed over 20 g of silica gel with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-c83c80cf0e7647598bb3f4daa7d94c66
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403806B1

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