Benzyl Bromide → HCID 10745912, compound

HRID 1106930Notes

Reaction equation

HRID 1106930 reaction equation
[C:1]([N:4]1[C@H:16]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]1[CH2:27][C:28]12[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2)(=[O:3])[CH3:2].[H-].[Na+].[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C=O)C.C(OCC)(=O)C>[C:1]([N:4]1[C@H:16]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:6]=2[C@H:5]1[CH2:27][C:28]12[CH2:29][CH:30]3[CH2:31][CH:32]([CH2:33][CH:34]([CH2:36]3)[CH2:35]1)[CH2:37]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86755367HCID 86755367, compound

Product 1

HCID 10745912HCID 10745912, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1R,3S)-benzyl 2-acetyl-1-(1-adamantyl)methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (6.3 g, 12.7 mmol) in dry DMF (50 ml) was added dropwise to a slurry of sodium hydride (60% dispersion in oil/0.56 g, 14 mmol) in dry DMF (20 ml) under nitrogen at room temperature. The reaction mixture was stirred for 15 minutes at room temperature to which was added dropwise a solution of benzyl bromide (1.6 ml, 13.5 mmol) in DMF (10 ml). The reaction was stirred for a further one hour, diluted with ethyl acetate (150 ml), washed successively with 2N HCl (150 ml), brine (3×150 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the product as a yellow foam which was used without further purification. (7.45 g, 100%).

Workup

  1. stirringThe reaction was stirred for a further one hour
  2. washwashed successively with 2N HCl (150 ml), brine (3×150 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-d14ab5bd6f5444459bd298619b017a96
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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