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

HRID 14311

反応式

HRID 14311 の反応式
[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]

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 45051747Lithium diisopropylamine

生成物 1

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

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-03f152eb106646e9b0d12632e1b86d0e
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

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