Tetrahydrofuran → tert-Butyl 3,4-dihydroxypiperidine-1-carboxylate

HRID 132874

반응식

HRID 132874 반응식
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])CC=CC[CH2:2]1.Cl([O-])(=O)=[O:15].[K+].[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O.[Os](=O)(=O)(=O)=O>[OH:19][CH:23]1[CH:22]([OH:15])[CH2:21][CH2:20][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2]1

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 6426889Potassium Chlorate2회HCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

생성물 1

HCID 22929427tert-Butyl 3,4-dihydroxypiperidine-1-carboxylate

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매2회HCID 962Water용매2회

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 21 g (115 mmol) of tert-butyl 3,6-dihydropyridine-1(2H)-carboxylate from Step A in 5 mL of tetrahydrofuran was added 300 mL of water, followed by 18 g (149 mmol) of potassium chlorate. Then a solution of 200 mg of osmium tetroxide in 30 mL of water was added slowly in portions. The mixture was stirred at 80° C. for 16 h. At this time, additional portions of potassium chlorate (11.2 g, 92 mmol) and osmium tetroxide (138 mg) were added, and stirring was continued at 80° C. for another 3.5 h. The reaction mixture was partitioned between diethyl ether and water. The aqueous phase was extracted with dichloromethane and then concentrated in vacuo. The resultant residue from the aqueous phase was extracted with tetrahydrofuran. The combined organic fractions were concentrated in vacuo, and the residue was purified by flash chromatography (silica gel, 0-5% methanol/dichloromethane) to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.93 (br s, 2H), 3.92 (m, 1H)-3.83 (m, 1H), 3.63 (m, 2H), 3.39 (m, 1H), 3.25 (m, 1H), 1.84 (m, 1H), 1.72 (m, 1H), 1.47 (s, 9H). LC/MS: 240 (M+1).

후처리

  1. stirringstirring
  2. waitwas continued at 80° C. for another 3.5 h
  3. customThe reaction mixture was partitioned between diethyl ether and water
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. concentrationconcentrated in vacuo
  6. extractionThe resultant residue from the aqueous phase was extracted with tetrahydrofuran
  7. concentrationThe combined organic fractions were concentrated in vacuo
  8. customthe residue was purified by flash chromatography (silica gel, 0-5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-0519e84b5b9543a68d8cf6cb537a22e7
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388019B2

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