1-Bromo-2-methylpropane → Quinolizidin-2-ylmethyl-1-isobutylindole-3-carboxylate

HRID 741564Notes

Reaction equation

HRID 741564 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].Br[CH2:25][CH:26]([CH3:28])[CH3:27]>>[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]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH:16]=1)=[O:14]

Participants

3

Reactant 2

HCID 65551-Bromo-2-methylpropaneHCID 131719520Quinolizidin-2-ylmethylindole-3-carboxylate

Product 1

HCID 131719528Quinolizidin-2-ylmethyl-1-isobutylindole-3-carboxylate

Procedure

eq-Quinolizidin-2-ylmethylindole-3-carboxylate (E9b) was alkylated with 1-bromo-2-methylpropane using the method in Example 18. The product was chromatographed on silica gel eluting initially with ether, then with ethyl acetate, to afford the title compound (E20) as a colourless oil. This was converted to its hydrochloride salt mp 174°-175° C. (acetone/ether).

Workup

  1. customThe product was chromatographed on silica gel eluting initially with ether

Sources & evidence

ORD record
ord-cde6ba34dbe54f17a57946b65f156353
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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