Water → [4-(Aminomethyl)phenyl]methanol

HRID 1509361Notes

Reaction equation

HRID 1509361 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 23132430[4-(Azidomethyl)phenyl]methanol

Product 1

HCID 6496943[4-(Aminomethyl)phenyl]methanolYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Azide 5 (1.96 g, 12.0 mmol) and PPh3 (6.50 g, 24.8 mmol, 2.05 eq) were dissolved in THF (25 ml) and heated at 60° C. for 1 hour. Water (4.5 ml, 248 mmol, 20 eq) was added and the reaction was heated overnight. The solvent was evaporated and the residue obtained was purified by flash chromatography (eluent DCM to 4:1 DCM/methanol saturated with NH3) to yield 6 as a white solid (1.44 g, 10.5 mmol, 85%). Rf=0.05 (9:1, DCM/MeOH sat. NH3); νmax=cm−1; 1H NMR (300 MHz, CDCl3) δ=7.35 (d, 3J(H,H)=8.4 Hz, 2H, ArCH α to CH2NH2), 7.30 (d, 3J(H,H)=8.4 Hz, 2H, ArCH α to CH2OH), 4.67 (s, 2H, CH2OH), 3.85 (s, 2H, CH2NH2), 1.68 (bs, 3H, OH, NH2); 13C NMR (75 MHz, CDCl3) δ=142.6 (ArCCH2NH2), 139.6 (ArCCH2OH), 127.3 (ArCH), 127.2 (ArCH), 65.0 (CH2OH), 46.2 (CH2NH2); HRMS (ESI+): m/z calculated for C8H12NO [M+H]+: 138.0913, found 138.0933.

Workup

  1. temperaturethe reaction was heated overnight
  2. customThe solvent was evaporated
  3. customthe residue obtained
  4. customwas purified by flash chromatography (eluent DCM to 4:1 DCM/methanol saturated with NH3)

Sources & evidence

ORD record
ord-d214715513464428bc61b3cc7df0d9e6
Source dataset
uspto-grants-2015_12
Patent number
US09222941B2

Reaction notes

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