Hydrochloric Acid → HCID 58188261, compound

HRID 1845117Notes

Reaction equation

HRID 1845117 reaction equation
[N:1]([C@@H:4]([C:7]1[CH:8]=[N:9][C:10]([CH:13]([F:15])[F:14])=[CH:11][CH:12]=1)[CH2:5][OH:6])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.Cl>C1COCC1>[NH2:1][C@@H:4]([C:7]1[CH:8]=[N:9][C:10]([CH:13]([F:15])[F:14])=[CH:11][CH:12]=1)[CH2:5][OH:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 58188209HCID 58188209, compound

Product 1

HCID 58188261HCID 58188261, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-2-azido-2-(6-(difluoromethyl)pyridin-3-yl)ethanol (1 g, 4.67 mmol) in 15 mL of THF was added PPh3 (2.45 g, 9.39 mmol). The resulting reaction mixture was stirred for 3 h, treated with 0.5 mL of water and stirred for 16 h. After completion of the reaction, the reaction mixture was treated with 2N HCl (15 mL) and extracted with EtOAc. The aqueous layer was treated with aq. NH3 and the volatiles were evaporated to afford a residue. Purification of the residue by column chromatography (small pad of neutral Al2O3, aq. NH3/MeOH/CH2Cl2, 1:14:85) afforded the title compound (0.74 g, 85% yield). MS: 189 [M+1]+; 1H-NMR (300 MHz, CD3OD): 8.72 (s, 1H), 8.09 (d, 1H, J=8.3 Hz), 7.75 (d, 1H, J=8.3 Hz), 6.73 (t, 1H, J=55.0 Hz), 4.39-4.43 (m 1H), 3.90 (dd, 1H, J=10.9, 4.7 Hz), 3.80 (dd, 1H, J=10.9, 6.2 Hz).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred for 16 h
  3. customAfter completion of the reaction
  4. extractionextracted with EtOAc
  5. additionThe aqueous layer was treated with aq. NH3
  6. customthe volatiles were evaporated
  7. customto afford a residue
  8. customPurification of the residue by column chromatography (small pad of neutral Al2O3, aq. NH3/MeOH/CH2Cl2, 1:14:85)

Sources & evidence

ORD record
ord-2005a321115c493d811df7a3aa577afd
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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