Hydrochloric Acid → HCID 68999097, compound

HRID 1909750Notes

Reaction equation

HRID 1909750 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]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:34].CCOCC>O1CCOCC1>[ClH:34].[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]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69003760HCID 69003760, compound

Product 1

HCID 68999097HCID 68999097, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 20 mL vial which contained a solution of (R)-2-[4-(4-Pyridin-4-yl-benzyl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (65 mg, 0.15 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 in vacuo to yield the title product (35 mg, 80%); LCMS; 97%, APCI+, Calcd: 344.5; Found m/z: 345.8 (M+1); 1H NMR (500 MHz, DMSO-d6); δ 1.66-1.76 (m, 1H), 1.84-2.02 (m, 2H), 2.06-2.15 (m, 1H), 3.14-3.26 (m, 2H), 3.87 (br, 1H), 4.00 (s, 2H), 4.09-4.19 (m, 1H), 4.21 (dd, J1=11.0, J2=4.0, 1H), 6.93 (d, J=8.5 Hz, 2H), 7.23 (d, J=8.5 Hz, 2H), 7.45 (d, J=8.0 Hz, 2H), 7.94 (d, J=8.5 Hz, 2H), 8.27 (d, J=6.0 Hz, 2H), 8.89 (d, J=6.0 Hz, 2H):

Workup

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

Sources & evidence

ORD record
ord-f14a5545f8694082afc4134a07e05c03
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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