Hydrochloric Acid → (S)-2-[4-(4-Chloro-benzyl)-phenoxymethyl]-pyrrolidine hydrochloride

HRID 1909636Notes

Reaction equation

HRID 1909636 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.Cl>O1CCOCC1>[ClH:28].[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:16][CH:17]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69003414(S)-2-[4-(4-Chloro-benzyl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68998035(S)-2-[4-(4-Chloro-benzyl)-phenoxymethyl]-pyrrolidine hydrochlorideYield 133.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the product from step 1 (3.55 g, 8.83 mmol) was added 4M HCl in dioxane (35 mL). The resulting mixture was stirred at ambient temperature overnight. The solvent was removed in vacuo. The crude product was triturated with ether and dried under reduced pressure to afford the title product (2.00 g, 67%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude product was triturated with ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-9c4d5ccb5fc947c0982cda3650be09cf
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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