Hydrochloric Acid → (R)-2-[4-(4-Fluoro-phenoxy)-phenoxymethyl]-pyrrolidine

HRID 749987Notes

Reaction equation

HRID 749987 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]([O:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.Cl>CO.C(OCC)C>[F:28][C:25]1[CH:26]=[CH:27][C:22]([O: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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69004867(R)-2-[4-(4-Fluoro-phenoxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59752924(R)-2-[4-(4-Fluoro-phenoxy)-phenoxymethyl]-pyrrolidineYield 113.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To the product from step 1 (271 mg, 0.699 mmol) in methanol (3 mL) was added 1M HCl in diethyl ether (15 mL) and the resulting mixture was stirred at rt for 7 h. The solvent was removed in vacuo to obtain the product as a solid (228 mg, 99%): MS; m/z 288 (M+H): LCMS (UV) 98%. 1H NMR (400 MHz, DMSO-d6) δ 1.70-1.76 (m, 1H), 1.89-1.99 (m, 2H), 2.01-2.14 (m, 1H), 3.18-3.23 (m, 2H), 3.87-3.90 (m, 1H), 4.12-4.16 (dd, 1H J1=8.4 Hz, J2=10.8 Hz), 4.21-4.25 (dd, 1H J1=4 Hz, J2=10.8 Hz), 6.96-6.99 (m, 2H), 7.014-7.016 (m, 4H), 7.17-7.22 (m, 2H), 9.1 (s, 1H), 9.7 (s, 1H)

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-46702de6079b4b2fa68b111049fd0c8f
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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