Hydrochloric Acid → 2-[4-((R)-1-Pyrrolidin-2-ylmethoxy)-phenyl]-isoindole-1,3-dione hydrochloride

HRID 2242880Notes

Reaction equation

HRID 2242880 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[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:32]>O1CCOCC1>[ClH:32].[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[C:22](=[O:31])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]2=[O:30])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58900146(R)-2-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 687038242-[4-((R)-1-Pyrrolidin-2-ylmethoxy)-phenyl]-isoindole-1,3-dione hydrochlorideYield 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 (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 title product (30 mg, 90%); LCMS; 98%, ESI+ Calcd: 322.3, found m/z: 323.6 (M+1); 1HNMR (400 MHz, DMSO-d6): δ 1.73-1.84 (m, 1H), 1.86-2.04 (m, 2H), 2.10-2.20 (m, 1H), 3.18-3.28 (m, 2H), 3.88-3.98 (m, 1H), 4.16-4.21 (m, 1H), 4.33 (dd, J=10.8 Hz, 3.6 Hz, 1H), 7.14 (dd, J=6.8 Hz, 2.0 Hz, 2H), 7.40 (dd, J=6.8 Hz, 2.4 Hz, 2H), 7.89-7.97 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-3f44a4fa52664544af2d89c41fbba5de
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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