Hydrochloric Acid → (S)-(3-(Azetidin-3-ylamino)pyrrolidin-1-yl)(phenyl)methanone

HRID 403287Notes

Reaction equation

HRID 403287 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([NH:12][C@H:13]2[CH2:17][CH2:16][N:15]([C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14]2)[CH2:9]1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[NH:8]1[CH2:9][CH:10]([NH:12][C@H:13]2[CH2:17][CH2:16][N:15]([C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:25])[CH2:14]2)[CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67288181(S)-tert-Butyl-3-((1-benzoylpyrrolidin-3-yl)amino)azetidine-1-carboxylate

Product 1

HCID 67288563(S)-(3-(Azetidin-3-ylamino)pyrrolidin-1-yl)(phenyl)methanone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 5d (0.96 g, 2.78 mmol) in MeOH (5 mL) was added HCl solution in dioxane (4M, 10 mL) at room temperature. The mixture was stirred at room temperature for 4 h. The solvent was removed by evaporation. Ether (50 mL) was added to the residue. The off-white solid was collected by filtration, washed with hexanes, and dried under vacuum. The crude compound 5e was used in the next reaction without further purification. MS m/z (M+H+) 246.0.

Workup

  1. customThe solvent was removed by evaporation
  2. additionEther (50 mL) was added to the residue
  3. filtrationThe off-white solid was collected by filtration
  4. washwashed with hexanes
  5. customdried under vacuum
  6. customThe crude compound 5e was used in the next reaction without further purification

Sources & evidence

ORD record
ord-60b883c7bd42414d99cde428f4ad3807
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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