Hydrochloric Acid → HCID 68831358, compound

HRID 747790Notes

Reaction equation

HRID 747790 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=1)=[O:7])(C)(C)C.Cl.[C:24]([C:26]1[CH:34]=[CH:33][C:29](C(O)=O)=[CH:28][CH:27]=1)#[N:25].CN1CCOCC1.ClC(OCC)=O>O1CCOCC1.CN(C)C=O.C(OCC)(=O)C>[C:24]([C:26]1[CH:34]=[CH:33][C:29]([C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@@H:9]2[CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)=[O:7])=[CH:28][CH:27]=1)#[N:25]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 120874-Cyanobenzoic acidHCID 68836373HCID 68836373, compound

Product 1

HCID 68831358HCID 68831358, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

70 mg (0.23 mmol) of 1-t-butoxycarbonyl-(2R)-2-[(3-cyanophenoxy)methyl]pyrrolidine was dissolved in a dioxane solution containing 4 N hydrogen chloride and then stirred at room temperature for 3 hours. The solvent was distilled off to obtain the crude de-t-butoxycarbonyl product. 38 mg (0.25 mmol) of 4-cyano-benzoic acid was dissolved in 3 ml of dimethylformamide, and 100 mg (1 mmol) of N-methyl morpholine and 25 mg (0.23 mmol) of ethyl chloroformate were added thereto and stirred at 0° C. for 5 minutes, and the crude de-t-butoxycarbonyl product was added thereto and stirred at room temperature for 2 hours. The reaction solution was treated in an ordinary manner with ethyl acetate as the extractant to obtain the title compound.

Workup

  1. distillationThe solvent was distilled off
  2. customto obtain the crude de-t-butoxycarbonyl product
  3. stirringstirred at 0° C. for 5 minutes
  4. additionthe crude de-t-butoxycarbonyl product was added
  5. stirringstirred at room temperature for 2 hours

Sources & evidence

ORD record
ord-2f8d50f1e2114c29942f1c9c1c61847d
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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