Tetrahydrofuran → Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 349100

반응식

HRID 349100 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(NC(C)C)(C)C.[Li].C1C=CC(N[S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])=CC=1.[O:37]1CCCC1>>[F:34][C:33]([F:36])([F:35])[S:30]([O:37][C:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH:12]=1)(=[O:32])=[O:31]

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 45051747Lithium diisopropylamine

생성물 1

HCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

반응 조건

온도
0 °C

실험 절차

To a −70° C. stirred solution of N-Boc-piperidone (500 mg, 2.5 mmol) in tetrahydrofuran (11 mL) was added lithium diisopropylamine (1.37 mL of a 2 M solution in tetrahydrofuran, 2.75 mmol). The reaction mixture was stirred for 2 h, warmed to 0° C., and N-phenyltriflamide (955 mg, 2.67 mmol) was added. The solution was allowed to warm to room temperature and was stirred for 12 h. The reaction mixture was concentrated under reduced pressure. Purification by flash column chromatography (3:1 hexanes/ethyl acetate) afforded tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (240 mg): 1H NMR (300 MHz, CDCl3) δ 5.77 (s, 1H), 4.05 (m, 2H), 3.63 (m, 2H), 2.45 (m, 2H), 1.48 (s, 9H).

후처리

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 12 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customPurification by flash column chromatography (3:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-b6d46ff08eb54cc6a88f9e326d850452
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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