3-Pyridinemethanol → Pyridin-3-ylmethyl 3-ethynylazetidine-1-carboxylate

HRID 1253492Notes

Reaction equation

HRID 1253492 reaction equation
C1N=CN([C:6]([N:8]2[CH:12]=N[CH:10]=[CH:9]2)=[O:7])C=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=1.[C:21](C1CNC1)#[CH:22].C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1>C1COCC1.C(OCC)(=O)C>[C:21]([CH:10]1[CH2:9][N:8]([C:6]([O:20][CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[O:7])[CH2:12]1)#[CH:22]

Participants

8

Reactant 5

HCID 75103-PyridinemethanolHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 866570513-Ethynylazetidine

Product 1

HCID 77231360Pyridin-3-ylmethyl 3-ethynylazetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of CDI (1.14 g, 7.02 mmol) in THF (15 ml) was added pyridine-3-methanol (0.68 ml, 7.0 mmol) at 0° C., and the reaction was stirred at room temperature for 1 hour. A solution of 3-ethynylazetidine (TFA salt) (250 mg, 1.40 mmol) and triethylamine (0.98 ml, 7.0 mmol) in THF (3 ml) was added to the reaction mixture, followed with DBU (0.42 ml, 2.8 mmol). After 3 hours, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, then dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel, eluting with methanol/ethyl acetate to give pyridin-3-ylmethyl 3-ethynylazetidine-1-carboxylate. LRMS (ESI) calculated for C12H13N2O2 [M+H]+, 217.1; found 217.1.

Workup

  1. waitAfter 3 hours
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with methanol/ethyl acetate

Sources & evidence

ORD record
ord-9d151a528eba4f739d2ca5e4e3728b8e
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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