Water → 2-Aminomethyl-5-benzyloxy-pyran-4-one

HRID 1846831Notes

Reaction equation

HRID 1846831 reaction equation
[N:1]([CH2:4][C:5]1[O:6][CH:7]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=[O:11])[CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][C:5]1[O:6][CH:7]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=[O:11])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 867256892-Azidomethyl-5-benzyloxy-pyran-4-one

Product 1

HCID 215247532-Aminomethyl-5-benzyloxy-pyran-4-oneYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-azidomethyl-5-benzyloxy-pyran-4-one (4) (30.0 g, 116.7 mmol) in tetrahydrofuran (500 mL) were added triphenyl phosphine (61.16 g, 233.46 mmol) and water (5.2 mL) and the mixture was refluxed for 16 h. After completion of the reaction, solvent was evaporated under reduced pressure, then it was purified by normal column chromatography to get (2-aminomethyl-5-benzyloxy-pyran-4-one (5) (13.0 g, 48.16%) as a brown solid.

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. customAfter completion of the reaction, solvent
  3. customwas evaporated under reduced pressure
  4. customit was purified by normal column chromatography

Sources & evidence

ORD record
ord-14385a93c4644af888351129071e8d2b
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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