Allyl bromide → HCID 19697572, compound

HRID 863309Notes

Reaction equation

HRID 863309 reaction equation
[H-].[K+].[C:3]([O:7][C:8]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]([CH2:20][OH:21])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:22](Br)[CH:23]=[CH2:24]>O1CCCC1>[C:3]([O:7][C:8]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]([CH2:20][O:21][CH2:24][CH:23]=[CH2:22])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 82127Potassium hydrideHCID 19697696HCID 19697696, compound

Product 1

HCID 19697572HCID 19697572, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of a potassium hydride suspension (20% in oil) is added to a solution of 0.6 g of 1-tert-butoxycarbonyl-3(R,S)-hydroxymethyl-1,2,3,4-tetrahydroquinoline in 7 ml of tetrahydrofuran at 0° C., the mixture is stirred for 30 min and 0.58 ml of allyl bromide is then added. After the mixture has been stirred at 0° C. for 45 min, it is worked up in the customary manner and the crude product is purified over 50 g of silica gel (mobile phase F). 1-Tert-butoxycarbonyl-3(R,S)-allyloxymethyl-1,2,3,4-tetrahydroquinoline is obtained as a colourless oil (Rf (F)=0.40), which is then reacted analogously to Example 20a). Purification by means of FC over 50 g of silica gel with methylene chloride as the mobile phase gives 3(R,S)-allyloxymethyl-1,2,3,4-tetrahydroquinoline: Rf (F)=0.40; MS: M+ =203.

Workup

  1. stirringAfter the mixture has been stirred at 0° C. for 45 min
  2. customthe crude product is purified over 50 g of silica gel (mobile phase F)

Sources & evidence

ORD record
ord-b99f9a1015684649b48c9e17d049c6ef
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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