Sodium hydride → Carbonic acid, 3-cyclopropyl-3-oxetanyl 2-pyridinyl ester

HRID 1852162노트

반응식

HRID 1852162 반응식
[H-].[Na+].[CH:3]1([C:6]2([OH:10])[CH2:9][O:8][CH2:7]2)[CH2:5][CH2:4]1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18](=O)[O:19]C1C=CC=CN=1>C1COCC1.CCOC(C)=O.[Cl-].[Na+].O>[C:18](=[O:19])([O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=1)[O:10][C:6]1([CH:3]2[CH2:5][CH2:4]2)[CH2:9][O:8][CH2:7]1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 2757370Carbonic acid di-2-pyridyl esterHCID 717427063-Cyclopropyloxetan-3-ol

생성물 1

HCID 70979138Carbonic acid, 3-cyclopropyl-3-oxetanyl 2-pyridinyl ester수율 18.8%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To a suspension of sodium hydride, 60% in mineral oil (315 mg, 7.88 mmol) in THF (20 mL) was added 3-cyclopropyloxetan-3-ol (750 mg, 6.57 mmol) at 0° C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl)carbonate (1421 mg, 6.57 mmol) in THF (20 mL) through a cannula. The formed slurry was stirred at 0° C. for 30 min. The slurry was warmed to rt and stirred for 2 h. The reaction was diluted with EtOAc followed by brine. The organic layer was collected, dried over MgSO4, filtered and evaporated to give the crude material. The crude material was purified via biotage (40 g column, 5-40% EtOAc:Hex) to give the expected product 3-cyclopropyloxetan-3-yl pyridin-2-yl carbonate (290 mg, 18.76% yield) as a clear thick oil. 1H NMR (400 MHz, CHLOROFORM-d) d 8.54-8.36 (m, 1H), 7.89-7.77 (m, 1H), 7.34-7.25 (m, 1H), 7.17 (d, J=8.3 Hz, 1H), 4.84 (d, J=8.5 Hz, 2H), 4.42 (d, J=8.3 Hz, 2H), 1.67-1.56 (m, 1H), 0.81-0.72 (m, 2H), 0.72-0.63 (m, 2H).

후처리

  1. stirringThe formed slurry was stirred at 0° C. for 30 min
  2. stirringstirred for 2 h
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude material
  8. customThe crude material was purified via biotage (40 g column, 5-40% EtOAc:Hex)

출처 및 근거

ORD 기록
ord-206f36f88ed14c05a1f080ffb013d0db
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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