Benzyl Bromide → HCID 22380664, compound

HRID 895650Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=3[CH3:23])[C:16](=[O:24])[NH:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:33]([N:15]1[CH2:14][C:11]2([CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[CH3:23])[C:16]1=[O:24])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1′-(tert-Butoxycarbonyl)-2,3-dihydro-5-methylspiro[isoquinoline-4(1H),4′-piperidin]-1-one (80.7 mg) was dissolved in toluene (1.6 ml), added with sodium hydroxide (powder, 34.2 mg), potassium carbonate (67.4 mg), tetrabutylammonium hydrogensulfate (8.3 mg) and benzyl bromide (44 μl) and stirred at 70° C. for 3 hours. The reaction mixture was added with water (2 ml) and extracted twice with dichloromethane (2 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=1:5) to obtain 86 mg of the title compound. Yield: 84%.

Workup

extractionextracted twice with dichloromethane (2 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=1:5)

Sources & evidence

ORD record: ord-64c644c1418241a0b64a72a53cdd8961
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916822B2

Reaction notes

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