1,4-Dioxane hydrochloride → HCID 117857727, compound

HRID 1483156Notes

Reaction equation

HRID 1483156 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[CH:30]=[CH:29][C:12]2[CH2:13][C@@H:14]3[C@H:19]([CH3:20])[C@:18]([CH3:21])([C:11]=2[CH:10]=1)[CH2:17][CH2:16][N:15]3C(OC(C)(C)C)=O)=[O:8].[ClH:37].O1CCOCC1>>[ClH:37].[CH3:1][O:2][C:3]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[CH:30]=[CH:29][C:12]2[CH2:13][C@@H:14]3[C@H:19]([CH3:20])[C@:18]([CH3:21])([C:11]=2[CH:10]=1)[CH2:17][CH2:16][NH:15]3)=[O:8]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 117857555HCID 117857555, compound

Product 1

HCID 117857727HCID 117857727, compoundYield 96%

Procedure

A mixture of (2R,6R,11R)-tert-butyl 8-((2,4-dimethoxybenzyl)carbamoyl)-6,11-dimethyl-1,2,5,6-tetrahydro-2,6-methanobenzo[d]azocine-3(4H)-carboxylate (4.00 g, 8.09 mmol) in 4N HCl/dioxane was stirred at ambient temperature overnight. The majority of the solvent was decanted and the residue washed with diethyl ether (500 mL). The resulting solid was dried under reduced pressure giving (2R,6R,11R)-N-(2,4-dimethoxybenzyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocine-8-carboxamide hydrochloride (3.35 g, 96% yield); LC/MS (M+H)+=395.5.

Workup

  1. customThe majority of the solvent was decanted
  2. washthe residue washed with diethyl ether (500 mL)
  3. customThe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-d6cc2b95d89045328d7d64ea1adcbbca
Source dataset
uspto-grants-2016_08
Patent number
US09416137B2

Reaction notes

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