3-Methylpiperidine → 3-Methyl-1-{[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}piperidine

HRID 38904

반응식

HRID 38904 반응식
CC1C=CC(S(O[CH2:12][C@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH3:27][CH:28]1[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]1>C(#N)C>[CH3:27][CH:28]1[CH2:33][CH2:32][CH2:31][N:30]([CH2:12][C@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:23]([CH3:26])(=[O:24])=[O:25])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)[CH2:29]1

참가 물질

4

반응물 2

HCID 790813-MethylpiperidineHCID 86652934[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

생성물 1

HCID 444694583-Methyl-1-{[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}piperidine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

A mixture of [(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.20 g, 0.5 mmol), 3-methylpiperidine (0.35 ml, 3 mmol) and ACN (2 ml) was heated under microwave radiation at 120° C. for 30 min. Purification on flash column chromatography (Isooctane/EtOAc/MeOH). Yield: 0.097 g, 85%. The amine was converted to the fumaric acid salt and crystallized from MeOH/(i-Pr)2O. M.p. 159° C. MS m/z (rel. intensity, 70 eV) 325 (M+, 1), 113 (83), 112 (bp), 69 (43), 55 (46). [α]=+50° (MeOH).

후처리

  1. customPurification on flash column chromatography (Isooctane/EtOAc/MeOH)
  2. customcrystallized from MeOH/(i-Pr)2O
  3. custom[α]=+50° (MeOH)

출처 및 근거

ORD 기록
ord-b456ce4360a84ba2ac3b3cb60427655f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524766B2

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