Triethylamine → 3-Pyrrolidinol, 1-[1-(diphenylmethyl)-3-azetidinyl]-

HRID 749436Notes

Reaction equation

HRID 749436 reaction equation
CS(O[CH:6]1[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:23]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24]1.C(N(CC)CC)C>C(#N)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][CH:6]([N:23]3[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24]3)[CH2:7]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 689780803-Pyrrolidinol, 1-[1-(diphenylmethyl)-3-azetidinyl]-Yield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Diphenylmethyl)azetidin-3-yl methanesulfonate (see J. Org. Chem.; 56; 1991; 6729; 310 mg, 0.98 mmol) was dissolved in acetonitrile (3.5 mL). Pyrrolidin-3-ol (104 mg, 1.2 mmol) and triethylamine (124 mg, 1.2 mmol) were added and the mixture was subjected to microwave single node heating for 10 minutes. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate. The solution was washed with water, dried over MgSO4 and then the solvent was evaporated. There was obtained 280 mg (93%) of 1-[1-(diphenylmethyl)azetidin-3-yl]pyrrolidin-3-ol as an oil. 1H NMR (300 MHz, CDCl3): 1.6-1.8 (m, 1H), 2.1-2.3 (m, 2H), 2.4-2.6 (m, 2H), 2.6-2.8 (m, 1H), 2.9-3.0 (m, 2H), 3.1-3.2 (m, 1H), 3.3-3.4 (m, 2H), 4.3 (m, 1H), 4.4 (s, 1H), 7.1-7.5 (m, 10H); LCMS: m/z 309 (M+1)+.

Workup

  1. temperatureheating for 10 minutes
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. dry with materialdried over MgSO4
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ddac7de83a114d488f2d0bac4776d50e
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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