Hydrochloric Acid → HCID 66738959, compound

HRID 1641434Notes

Reaction equation

HRID 1641434 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]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:26]>O1CCOCC1>[ClH:26].[NH: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]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59660701HCID 59660701, compound

Product 1

HCID 66738959HCID 66738959, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 20 mL vial which contained a solution of (R)-2-(4-Pyrrol-1-yl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 1 (220 mg, 0.66 mmol) in dioxane (2 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 from MeOH-ether to yield the desired product (158 mg, 89%); 1HNMR (400 MHz, CDCl3) 7.52 (d, J=9.2 Hz, 2H), 7.27 (t, J=2.0 Hz, 2H), 7.07 (d, J=9.2 Hz, 2H), 6.23 (t, J=2.0 Hz, 2H), 4.28 (dd, J1=10.4 Hz, J2=3.6 Hz, 1H), 4.12-4.17 (m, 1H), 3.86-3.96 (m, 1H), 3.18-3.27 (m, 2H), 2.06-2.16 (m, 1H), 1.86-2.02 (m, 2H), 1.68-1.78 (m, 1H); LCMS; m/z (ESI+ 243.5, M+1); 93%.

Workup

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

Sources & evidence

ORD record
ord-a01db83c753a406683da58259e505f36
Source dataset
uspto-grants-2012_02
Patent number
US08115005B2

Reaction notes

Loading…