Isopropyl iodide → Quinolizidin-2-ylmethyl-1-isopropylindole-3-carboxylate

HRID 741562Notes

Reaction equation

HRID 741562 reaction equation
[CH2:1]1[CH:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH:2]1[CH2:11][O:12][C:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:14].[CH3:24][C:25](C)([O-])[CH3:26].[K+].IC(C)C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH2:1]1[CH:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH:2]1[CH2:11][O:12][C:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH:25]([CH3:26])[CH3:24])[CH:16]=1)=[O:14]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 10340Sodium CarbonateHCID 23665647Potassium tert-butoxideHCID 131719520Quinolizidin-2-ylmethylindole-3-carboxylate

Product 1

HCID 131719526Quinolizidin-2-ylmethyl-1-isopropylindole-3-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of eq-quinolizidin-2-ylmethylindole-3-carboxylate (E9b) (320 mg, 1.08 mmole) in dry THF (15 ml) at room temperature under nitrogen was treated with potassium t-butoxide (125 mg, 1.1 mmole) and stirred for 20 minutes. The solution was then treated with 2-iodopropane (0.11 ml, 1.1 mmole) and stirred for 18 h. The reaction mixture was treated with 10% Na2CO3 solution (25 ml) and extracted with ethyl acetate (2×50 ml). The combined extracts were dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting initially with ether, then with ethyl acetate, to afford the title compound (E18) as a colourless oil (240 mg, 63%). This was converted to the hydrochloride salt mp 235°-238° C. (acetone).

Workup

  1. stirringstirred for 18 h
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed on silica gel eluting initially with ether

Sources & evidence

ORD record
ord-3e72e1136c574e2982f0ee8fe26b06c9
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

Loading…