Hydrochloric Acid → (4-Iodo-phenyl)-[4-((R)-1-pyrrolidin-2-ylmethoxy)-phenyl]-methanone

HRID 750065Notes

Reaction equation

HRID 750065 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]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.Cl.CCOCC>O1CCOCC1>[I:28][C:25]1[CH:26]=[CH:27][C:22]([C: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)=[O:29])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 44221510(R)-2-[4-(4-Iodo-benzoyl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69001731(4-Iodo-phenyl)-[4-((R)-1-pyrrolidin-2-ylmethoxy)-phenyl]-methanoneYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 20 mL vial which contained a solution of the product from step 2 (25 mg, 0.05 mmol) in dioxane (1 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 reduced to 1 mL and ether (15 mL) was added to this vial. The resulting solid was filtered out and dried under vacuo to yield the title product (16 mg, 80%); LCMS; 100% ESI+Calcd: 407.3. found m/z: 408.5 (M+1). 1H NMR (500 NM, DMSO-d6); δ 1.71-1.80 (m, 1H), 1.82-2.06 (m, 2H), 2.10-2.20. (m, 1H), 3.16-3.30 (m, 2H), 3.90-4.00 (m, 1H), 4.23-4.27 (m, 1H), 4.38 (dd, J1=10.0 Hz, J2=2.5 Hz, 1H), 7.14 (d, J=8.5 Hz, 2H), 7.46 (d, J=7.5 Hz, 2H), 7.78 (d, J=9.0 Hz, 2H), 7.95 (d, J=8.0 Hz, 2H):

Workup

  1. additionwas added to this vial
  2. filtrationThe resulting solid was filtered out
  3. customdried under vacuo

Sources & evidence

ORD record
ord-60804eaa3ab24f9fa38f40af3982a5fd
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

Loading…