2-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one → methyl 3-{(4aRS,8SR,8aRS)-1-[2-(3,4-dichlorophenyl)acetyl]-8-(pyrrolidin-1-yl)-perhydroquinoxalin-4-yl}-3-oxopropionate

HRID 1876812Notes

Reaction equation

HRID 1876812 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]3[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[NH:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl-].[CH3:28][O:29][C:30](=[O:35])[CH2:31][C:32](O)=[O:33]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]3[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[N:15]([C:32](=[O:33])[CH2:31][C:30]([O:29][CH3:28])=[O:35])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 687760732-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-oneHCID 86615040Malonic acid methylester chloride

Product 1

HCID 68777945methyl 3-{(4aRS,8SR,8aRS)-1-[2-(3,4-dichlorophenyl)acetyl]-8-(pyrrolidin-1-yl)-perhydroquinoxalin-4-yl}-3-oxopropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, 2-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one (101 mg, 0.26 mmol) was dissolved in absolute CH2Cl2 (13 ml) and malonic acid monomethyl ester chloride (42 mg, 0.31 mmol) was added dropwise. The mixture was stirred at room temperature overnight and then evaporated in vacuo. The residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 9.5:0.5:0.05, l=15 cm, V=5 ml). A yellowish resin was obtained.

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 9.5:0.5:0.05, l=15 cm, V=5 ml)
  3. customA yellowish resin was obtained

Sources & evidence

ORD record
ord-f2377efdd0c04fc2a6d39bf3ec320f22
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Reaction notes

Loading…