Allyl bromide → HCID 68912516, compound

HRID 870360Notes

Reaction equation

HRID 870360 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]2[C@H:8]3[C@H:13]([CH2:14][CH2:15][C:6]=2[CH:5]=1)[NH:12][CH2:11][CH2:10][CH2:9]3)([O-:3])=[O:2].[CH2:18](Br)[CH:19]=[CH2:20]>C1COCC1>[CH2:20]([N:12]1[C@@H:13]2[C@H:8]([C:7]3[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[CH2:15][CH2:14]2)[CH2:9][CH2:10][CH2:11]1)[CH:19]=[CH2:18]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 68911952HCID 68911952, compound

Product 1

HCID 68912516HCID 68912516, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

(4aS,10bS)-8-Nitro-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline (0.50 g, 1.51 mmol) was dissolved in THF (30 mL) and allyl bromide (0.40 g, 3.30 mmol) added. The solution was stirred at 50° C. for 8 h, room temperature for 18 h and then evaporated. The residue was partitioned between ethyl acetate and NaOH (2M), and the organic phase separated and dried over MgSO4. The filtered solution was concentrated and separated by column chromatography (dichloromethane: 0-3% MeOH) to give the product as a yellow oil (0.40 g, 97%).

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate and NaOH (2M)
  3. customthe organic phase separated
  4. dry with materialdried over MgSO4
  5. concentrationThe filtered solution was concentrated
  6. customseparated by column chromatography (dichloromethane: 0-3% MeOH)

Sources & evidence

ORD record
ord-af79cfcb27554cdf8d3382ff276c7951
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

Loading…