1,4-Dioxane hydrochloride → (S)-benzyl 2-(4-aminophenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 44453

Reaction equation

HRID 44453 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[O:17])=[CH:11][CH:10]=1)=O)(C)(C)C.O1CCOCC1.Cl>O1CCOCC1>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59396122(S)-benzyl 2-(4-(tert-butoxycarbonylamino)phenylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 59396116(S)-benzyl 2-(4-aminophenylcarbamoyl)pyrrolidine-1-carboxylateYield 94.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the Product from Example 3A (0.245 g, 0.56 mmol) in dioxane (5 mL) was added 4M HCl dioxane (2.8 mL, 11.2 mol) and the mixture was stirred at ambient temperature for 17 hours. The mixture was concentrated and azeotroped with toluene to give a tan solid (0.18 g, 86%).

Workup

  1. concentrationThe mixture was concentrated
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-2fb70fcb6ee44d94841669e1f407e784
Source dataset
uspto-grants-2013_09
Patent number
US08541424B2

Linked notes

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