8-(4-(Methylsulfonyl)phenyl)-1,4-dioxa-8-azaspiro[4.5]decane → 1-(4-Methanesulfonylphenyl)piperidin-4-one

HRID 329928

반응식

HRID 329928 반응식
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].OS(O)(=O)=O.O1CCCC1>O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:20][CH2:19][C:14](=[O:15])[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

참가 물질

4

반응물 2

HCID 42563608-(4-(Methylsulfonyl)phenyl)-1,4-dioxa-8-azaspiro[4.5]decaneHCID 68124251Sulfuric acid tetrahydrofuran

생성물 1

HCID 141563991-(4-Methanesulfonylphenyl)piperidin-4-one수율 91%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 12.97 g (0.0436 mol) of the ketal of (A) and 200 ml of 10% H2SO4 /tetrahydrofuran (2:1) solution is stirred at 60°-70° C. for 4 hrs and is then allowed to stand at room temperature for 3 days. The mixture is diluted with water and extracted with methylene chloride. The combined extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo. Trituration with ethyl ether gives 10.07 g (91%) of title compound as a white solid: m.p. 183°-185° C.; IR (KBr) 3410, 1710, 1585, and 1160 cm-1 ; NMR (CDCl3) δ 7.79 (d, 2H), 6.98 (d, 2H), 3.79 (t, 4H), 3.04 (s, 3H), and 2.61 (t, 4H).

후처리

  1. waitto stand at room temperature for 3 days
  2. extractionextracted with methylene chloride
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-27e484b9bda6452486b50e00b32842b2
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894374

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