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

HRID 403629Notes

Reaction equation

HRID 403629 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4f6187ade87041f4be0f0c76413437d2
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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