1,2,3,4-Tetrahydrocarbazole → 6-(1,2,3,4-Tetrahydrocarbazol-9-yl)hexanoic acid ethyl ester

HRID 403627

반응식

HRID 403627 반응식
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CS(C)=O>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][N:12]1[C:13]2[CH2:1][CH2:2][CH2:3][CH2:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:30]

참가 물질

5

반응물 3

HCID 136641,2,3,4-TetrahydrocarbazoleHCID 117544Ethyl 6-bromohexanoateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 683805226-(1,2,3,4-Tetrahydrocarbazol-9-yl)hexanoic acid ethyl ester수율 32.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
110 °C

실험 절차

A RB flask fitted with reflux condenser containing tetrahydrocarbazole (1.71 g, 10.0 mol) was dissolved in DMSO (30 mL), treated with potassium tert-butoxide (1M solution in THF, 12 mL) and stirred at 110° C. for 20 min. Ethyl 6-bromohexanoate (1.67 mL, 10.0 mmol) was added and the mixture stirred at 110° C. for 60 min. The reaction was quenched with a 1:1 brine:water solution (120 mL) and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. Purification by column chromatography (25% ethyl acetate in hexane) afforded the title compound (1.01 g, 32%). 1H NMR (400 MHz, CDCl3): δ 7.52 (m, 1H), 7.27 (m, 1H), 7.19 (m, 1H), 7.12 (m, 1H), 4.18 (q, 2H, J=7.1 Hz), 4.04 (t, 2H, J=7.4 Hz), 2.78-2.73 (m, 4H), 2.33 (t, 2H, J=7.5 Hz), 2.00-1.92 (m, 4H), 1.80-1.75 (m, 2H), 1.72-1.66 (m, 2H), 1.42 (m, 2H), 1.30 (t, 3H, J=6.9 Hz). ESI-HRMS (m/z): [M+H]+ calcd. for C20H27NO2, 314.2115. found, 314.2103.

후처리

  1. customA RB flask fitted
  2. temperaturewith reflux condenser
  3. stirringthe mixture stirred at 110° C. for 60 min
  4. customThe reaction was quenched with a 1:1 brine
  5. extractionwater solution (120 mL) and extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification by column chromatography (25% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-c154693568274938b9529162e27787ba
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748451B2

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