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

HRID 1909694Notes

Reaction equation

HRID 1909694 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 199%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the product from step 1 (1.64 g, 4.1 mmol) was added 4M HCl in dioxane (45 mL) and the resulting mixture was stirred at rt for 5 h. The solvent was removed in vacuo to obtain the title product (1.38 g, 99%): 1H NMR (400 MHz, DMSO-d6) δ 1.67-2.15 (m, 5H), 3.17-3.21 (m, 2H), 3.88 (s, 2H), 4.07-4.12 (dd, 1H J1=8.4 Hz, J2=10.8 Hz), 4.18-4.22 (dd, 1H J1=3.6 Hz, J2=10.8 Hz), 6.91 (d, 2H, J=8.8 Hz), 7.16 (d, 2H, J=8.8 Hz), 7.22 (d, 2H, J=8.8 Hz); 7.33 (d, 2H, J=8.8 Hz)

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-12d2b6474d1e46e69a7d525127f745b8
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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