Hydrochloric Acid → (R)-2-(4-Benzyloxy-phenoxymethyl)-pyrrolidine hydrogen chloride salt

HRID 750032Notes

Reaction equation

HRID 750032 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][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:29]>O1CCOCC1>[ClH:29].[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][CH:17]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68999348(R)-2-(4-Benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69000219(R)-2-(4-Benzyloxy-phenoxymethyl)-pyrrolidine hydrogen chloride saltYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 20 mL vial which contained a solution of the product from step 1 (40 mg, 0.1 mmol) in dioxane (0.5 mL) was added HCl (4 N in dioxane 2 mL) at 0° C. The mixture was allowed to warm to rt and stir at rt for 16 h. The solvent was removed and the crude was purified by recrystallization with MeOH-ether to yield the title product (27 mg, 90%); LCMS; 95% ESI+, Calcd: 238.4 m/z. Found: 284.4 (M+1) m/z. 1H NMR (400 MHz, DMSO-d6); δ 1.68-1.76 (m, 1H), 1.86-2.04 (m, 2H), 2.07-2.14 (m, 1H), 3.20 (br, 2H), 3.87 (br, 1H), 4.05 (dd, J1=10.4 Hz, J2=8.4 Hz, 1H), 4.18 (dd, J/=10.4 Hz, J2=3.6 Hz, 1H), 5.05 (s, 2H), 6.91-6.99 (m, 4H), 7.30-7.44 (m, 5H):

Workup

  1. customThe solvent was removed
  2. customthe crude was purified by recrystallization with MeOH-ether

Sources & evidence

ORD record
ord-7c7de1f57ce245dc85786b0caa7d7d7b
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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