Dichloromethane → HCID 68621897, compound

HRID 1244694Notes

Reaction equation

HRID 1244694 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]1[CH:25]([N:26]([C:31](=[O:34])[CH:32]=C)[CH2:27][CH2:28][CH:29]=C)[CH2:24][N:11]2[CH2:12][CH2:13][C:14]3[C:19]([CH:10]2[CH2:9]1)=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=3)([CH3:4])([CH3:3])[CH3:2].[Cl:36][CH2:37][Cl:38]>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[CH2:37]([Cl:38])[Cl:36].[CH3:1][OH:5].[NH4+:7].[OH-:5].[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]1[CH:25]([N:26]2[C:31](=[O:34])[CH:32]=[CH:29][CH2:28][CH2:27]2)[CH2:24][N:11]2[CH2:12][CH2:13][C:14]3[C:19]([CH:10]2[CH2:9]1)=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=3)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 68620864HCID 68620864, compound

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 68621897HCID 68621897, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

Tetraisopropyl orthotitanate (7.6 mg, 27 μmol) and Bis(tricyclohexylphosphine)-benzylideneruthenium(IV)dichloride (11 mg, 13 μmol) were added to a solution of (RS,RS,RS)-[3-(acryloyl-but-3-enyl-amino)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl]-carbamic acid tert-butyl ester (65 mg, 0.13 mmol) in dichloromethane (2.5 mL). The reaction mixture was stirred 45 min at r.t., then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, CH2Cl2/MeOH/NH4OH 95:5:0.25) afforded the title compound (59 mg, 96%). White solid, MS (ISP) 458.4 (M+H)+.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-8a325fb0466d405c82283c57d6929495
Source dataset
uspto-grants-2006_10
Patent number
US07122555B2

Reaction notes

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