1,4-Dioxane hydrochloride → Trans-4-[4-(4-Chloro-phenyl)-[1,4]diazepan-1-yl]-pyrrolidin-3-ol

HRID 241339Notes

Reaction equation

HRID 241339 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([N:14]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([N:17]2[CH2:18][CH2:19][CH2:20][N:14]([C@@H:10]3[CH2:9][NH:8][CH2:12][C@H:11]3[OH:13])[CH2:15][CH2:16]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57982392trans-3-[4-(4-Chloro-phenyl)-[1,4]diazepan-1-yl]4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57982428Trans-4-[4-(4-Chloro-phenyl)-[1,4]diazepan-1-yl]-pyrrolidin-3-olYield 151.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-3-[4-(4-Chloro-phenyl)-[1,4]diazepan-1-yl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.820 g, 2.08 mmol) in methylene chloride (1 mL) was added 4 N HCl/dioxane (10 mL, 40 mmol). The solution was stirred at rt for 1 hour, upon which a brown precipitate formed. The reaction was concentrated in vacuo to yield 0.930 g (˜100%) of the title compound. ESI-MS m/z: 296 (M+1), FAS method rt: 0.83 min.

Workup

  1. customformed
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-8038e9ba8460486eb7279f1597352eb4
Source dataset
uspto-grants-2014_02
Patent number
US08648197B2

Reaction notes

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