Sodium hydride → 6-(2-Methyl-1,2,3,4-tetrahydro-b-carbolin-9-yl)hexanoic acid ethyl ester

HRID 1970812ノート

反応式

HRID 1970812 の反応式
[CH3:1][N:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH2:3]1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:5]1[C:4]2[CH2:3][N:2]([CH3:1])[CH2:14][CH2:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:27]

参加物

4

反応物 3

HCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 1218962-Methyl-1,2,3,4-tetrahydro-beta-carboline

生成物 1

HCID 668730706-(2-Methyl-1,2,3,4-tetrahydro-b-carbolin-9-yl)hexanoic acid ethyl ester収率 52.6%

反応条件

温度
60 °C

実験手順

A round bottom flask fitted with reflux condenser containing 2-methyl-2,3,4,9-tetrahydro-1H-β-carboline (16) (0.20 g, 1.1 mmol), and sodium hydride (60% by wt. in mineral oil, 0.055 g, 1.35 mmol) was vacuum purged and filled with argon, followed by addition of DMF (4 mL). After stirring at 60° C. for 20 min, ethyl 6-bromo-hexanoate (0.24 g, 1.1 mmol) was added and the mixture was stirred at 60° C. for 6 h. The reaction was quenched by addition of water (30 mL), transferred to a separatory funnel and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2×20 mL), dried (Na2SO4) and concentrated. The product was purified by MPCC (0-10% gradient of MeOH in CH2Cl2), giving 190 mg of 6-(2-methyl-1,2,3,4-tetrahydro-b-carbolin-9-yl)hexanoic acid ethyl ester.

後処理

  1. customA round bottom flask fitted
  2. temperaturewith reflux condenser
  3. custompurged
  4. additionfilled with argon
  5. additionfollowed by addition of DMF (4 mL)
  6. stirringthe mixture was stirred at 60° C. for 6 h
  7. customThe reaction was quenched by addition of water (30 mL)
  8. customtransferred to a separatory funnel
  9. extractionextracted with ethyl acetate (3×20 mL)
  10. washThe combined organic layers were washed with brine (2×20 mL)
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated
  13. customThe product was purified by MPCC (0-10% gradient of MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-3a95e79cd70146ab994f1a8353e782ee
出典データセット
uspto-grants-2013_04
特許番号
US08431538B2

反応ノート

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