Pyrrolidine → 1-[1-(Diphenylmethyl)-3-methyl-3-azetidinyl]pyrrolidine

HRID 1366578Notes

Reaction equation

HRID 1366578 reaction equation
CS(O[C:6]1([CH3:23])[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>C(O)(C)C>[C:11]1([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:9][C:6]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)([CH3:23])[CH2:7]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 100652951-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

Product 1

HCID 669361071-[1-(Diphenylmethyl)-3-methyl-3-azetidinyl]pyrrolidineYield 65.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(diphenylmethyl)-3-methyl-3-azetidinyl methanesulfonate (1.55 g, 4.68 mmol) (J. Med. Chem. 1993, 36, 801-810) and pyrrolidine (3.86 ml, 46.68 mmol) in isopropanol (15 ml) was heated to 70° C. overnight. After cooling to room temperature, the mixture was concentrated to dryness in vacuo. Water (100 ml) was added, and the mixture was extracted with dichloromethane (2×100 ml). The combined organic solution was washed with brine (60 ml), dried (Na2SO4) and concentrated. The residue was purified via RP-HPLC to provide 1-[1-(diphenylmethyl)-3-methyl-3-azetidinyl]pyrrolidine (0.94 g, 65%). LCMS: (M+H)+: 307.2.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated to dryness in vacuo
  3. additionWater (100 ml) was added
  4. extractionthe mixture was extracted with dichloromethane (2×100 ml)
  5. washThe combined organic solution was washed with brine (60 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified via RP-HPLC

Sources & evidence

ORD record
ord-3744fd5d62494a7f87604bb3b766d15c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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