1,4-Dioxane hydrochloride → (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine

HRID 2103657Notes

Reaction equation

HRID 2103657 reaction equation
O1CCOCC1.Cl.C(OC([NH:15][CH2:16][C:17]([NH:19][C@@H:20]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH2:21]1)=[O:18])=O)(C)(C)C>CO>[NH2:15][CH2:16][C:17]([NH:19][C@@H:20]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[CH2:21]1)=[O:18]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 53939240(R)-3-(N-(tert-butoxycarbonyl)glycyl)amino-1-(4-chlorobenzyl)pyrrolidine

Product 1

HCID 54551710(R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4M HCl dioxane (38 mL) solution was added to the methanol (60 mL) solution of the (R)-3-{N-(tert-butoxycarbonyl)glycyl}amino-1-(4-chlorobenzyl)pyrrolidine (5.39 g, 14.7 mmol). The solution was stirred at room temperature for 2 hours. The reaction mixture was concentrated and then mixed with a 2M NaOH solution (80 mL). The mixture was extracted with dichloromethane (80 mL×3), and the extracts were combined, dried over anhydrous sodium sulfate, and then concentrated. The (R)-3-(glycylamino)-1-(4-chlorobenzyl)pyrrolidine (3.374 g, 86%) was obtained by column chromatography (SiO2, AcOEt/EtOH/Et3N=90/5/5).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionmixed with a 2M NaOH solution (80 mL)
  3. extractionThe mixture was extracted with dichloromethane (80 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8954b37827de43ea8db3a4f65930a7ad
Source dataset
uspto-grants-2009_08
Patent number
US07576117B1

Reaction notes

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