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

HRID 403627

反応式

HRID 403627 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c154693568274938b9529162e27787ba
出典データセット
uspto-grants-2014_06
特許番号
US08748451B2

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