Dichloromethane methanol ammonium hydroxide → HCID 11394279, compound

HRID 1244688Notes

Reaction equation

HRID 1244688 reaction equation
[C:1]([O:5]C(=O)[NH:7][CH:8]1[CH:25]([C:26]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:27])[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)(C)(C)C.[CH2:34]([Cl:36])[Cl:35].C[OH:38].[NH4+].[OH-]>Cl>[CH2:34]([Cl:36])[Cl:35].[CH3:1][OH:5].[NH4+:7].[OH-:38].[NH2:7][CH:8]1[CH:25]([C:26]([N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)=[O:27])[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

Participants

5

Reactant 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 68622093HCID 68622093, compound

Product 2

HCID 11394279HCID 11394279, compoundYield 74%HCID 21896990Dichloromethane methanol ammonium hydroxide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (RS,RS,RS)-[9,10-dimethoxy-3-(pyrrolidine-1-carbonyl)-1,3,4,6,7,11b-hexahydro-2H-pyrido [2,1-a]isoquinolin-2-yl]-carbamic acid tert-butyl ester (55 mg, 0.12 mmol) in hydrogen chloride solution (4 M in dioxane, 1 mL) was stirred 1 h at r.t., then neutralized with CH2Cl2/MeOH/NH4OH 90:10:0.25 and evaporated. Chromatography of the residue (SiO2, CH2Cl2/MeOH/NH4OH 90:10:0.25) afforded the title compound (32 mg, 74%). Off-white foam, MS (ISP) 359.6 (M+).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-51052bb8a0b543d0ae874df02b990122
Source dataset
uspto-grants-2006_10
Patent number
US07122555B2

Reaction notes

Loading…