Methyl bromoacetate → HCID 68771915, compound

HRID 2382177Notes

Reaction equation

HRID 2382177 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:3]1.Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].C(N(C(C)C)CC)(C)C>CC#N>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:5][CH2:6][N:7]1[CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 68772034HCID 68772034, compound

Product 1

HCID 68771915HCID 68771915, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3R)-3-methyl-1-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazine (620 mg, 2.537 mmol) in MeCN was added methyl 2-bromoacetate (466 mg, 3.044 mmol) followed by diisopropylethylamine (0.884 ml, 5.074 mmol). The reaction mixture was stirred at rt for 5 h. The solvent was evaporated under high vacuum and the residue was loaded on column (SiO2, hexane to hexane/EtOAc=100:10 to 100:20 to 100:30 to 100:40) to give methyl 2-((R)-2-methyl-4-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)piperazin-1-yl)acetate (800 mg, 99.6% yield) as a gum.

Workup

  1. customThe solvent was evaporated under high vacuum

Sources & evidence

ORD record
ord-d09ee6b6c94b483cb62d21d25eb0a7a7
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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