Hydrochloric Acid → HCID 59752889, compound

HRID 1909748Notes

Reaction equation

HRID 1909748 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]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.Cl.CCOCC>O1CCOCC1>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69001441HCID 69001441, compound

Product 1

HCID 59752889HCID 59752889, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 20 mL vial which contained a solution of (S)-2-[4-(4-morpholin-4-yl-benzyl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (100 mg, 0.2 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 (70 mg, 80%); LCMS; 90%, ESI+ Calcd: 352.5, found m/z: 353.7 (M+1); 1H NMR (400 MHz, DMSO-d6); δ 1.66-1.76 (m, 1H), 1.84-2.02 (m, 2H), 2.04-2.14 (m, 1H), 3.05-3.24 (m, 4H), 3.73-4.12 (m, 10H), 4.19 (dd, J1=10.8 Hz, J2=3.6 Hz, 1H), 6.91 (d, J=8.4 Hz, 2H), 7.20 (m, 6H):

Workup

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

Sources & evidence

ORD record
ord-6a2b108ccff745aa8cda405938450918
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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