Hydrochloric Acid → Ethyl 2-(Benzyloxy)-9-hydroxy-6,7-dihydropyrido[1,2-a]indole-8-carboxylate

HRID 515738Notes

Reaction equation

HRID 515738 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:13]([C:26](OCC)=[O:27])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH2:18][CH2:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:26]([OH:27])[C:13]1=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 67248905ethyl 5-(benzyloxy)-1-(4-ethoxy-4-oxobutyl)-1H-indole-2-carboxylate

Product 1

HCID 67249262Ethyl 2-(Benzyloxy)-9-hydroxy-6,7-dihydropyrido[1,2-a]indole-8-carboxylateYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 5-(benzyloxy)-1-(4-ethoxy-4-oxobutyl)-1H-indole-2-carboxylate (1 g, 2.442 mmol) in THF was added a 1 M solution of KOtBu in THF (3.17 mL, 3.17 mmol) at 0° C. The reaction mixture was stirred at that temperature for 2 h, poured into 1 N HCl aqueous solution, extracted with ethyl acetate. The combined organics were washed with water, dried over Na2SO4, and concentrated to give the title compound (850 mg) without further purification. LCMS m/z=364.3 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ec0c580a786740cda987500e9266e9b1
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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