1-Acetoxy-2-bromoethane → HCID 66758364, compound

HRID 242603Notes

Reaction equation

HRID 242603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:35])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[N:27][C:22]=4[CH2:21][O:20][C:19]4[CH:28]=[CH:29][C:30]([OH:32])=[CH:31][C:18]3=4)[CH2:10][C:9]2([CH3:34])[CH3:33])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:39][CH2:40][O:41][C:42](=[O:44])[CH3:43]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:35])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[N:27][C:22]=4[CH2:21][O:20][C:19]4[CH:28]=[CH:29][C:30]([O:32][CH2:39][CH2:40][O:41][C:42](=[O:44])[CH3:43])=[CH:31][C:18]3=4)[CH2:10][C:9]2([CH3:33])[CH3:34])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 66757704HCID 66757704, compound

Product 1

HCID 66758364HCID 66758364, compound

Procedure

To a solution of 5-{3-[4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidin-1-yl]-propylidene}-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-ol (64.5 mg, 0.131 mmol) in N,N-dimethylormamide (2.5 ml) was added sodium hydride (6 mg, 0.158 mmol), 60% dispersion in mineral oil, then acetic acid 2-bromo-ethyl ester (17 μl, 0.158 mmol). The reaction stirred at room temperature overnight under a nitrogen atmosphere. The reaction was quenched the following day with water and diluted with ethyl acetate. The organic layer was washed twice with water, then brine. After the organic layer was dried over magnesium sulfate the solvent was distilled off under reduced pressure to give the title compound, 132 mg (100%).

Workup

  1. customThe reaction was quenched the following day with water
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed twice with water
  4. dry with materialAfter the organic layer was dried over magnesium sulfate the solvent
  5. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-ed4730941f864efe9f5be6c87f5da442
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

Loading…