tert-Butyl bromoacetate → HCID 68736144, compound

HRID 2382180Notes

Reaction equation

HRID 2382180 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:3]1.Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(N(C(C)C)CC)(C)C>CC#N>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:5][CH2:6][N:7]1[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 68735476HCID 68735476, compound

Product 1

HCID 68736144HCID 68736144, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3R)-3-methyl-1-(2-phenylcyclohexyl)piperazine (900 mg, 3.48 mmol) (crude) in MeCN was added tert-butyl 2-bromoacetate (0.815 g, 4.18 mmol) followed by diisopropylethylamine (1.21 ml, 6.97 mmol). The reaction 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 tert-butyl 2-((R)-2-methyl-4-(2-phenylcyclohexyl)piperazin-1-yl)acetate (1.16 g, 89.4% yield) as a gum.

Workup

  1. customThe solvent was evaporated under high vacuum

Sources & evidence

ORD record
ord-c2d343a1759946159102539a8e79ae29
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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