Hydrochloric Acid → HCID 58188209, compound

HRID 1845116Notes

Reaction equation

HRID 1845116 reaction equation
[N:1]([C@@H:4]([C:14]1[CH:15]=[CH:16][C:17]([CH:20]([F:22])[F:21])=[N:18][CH:19]=1)[CH2:5][O:6][Si](C(C)(C)C)(C)C)=[N+:2]=[N-:3].Cl>CCO>[N:1]([C@@H:4]([C:14]1[CH:19]=[N:18][C:17]([CH:20]([F:21])[F:22])=[CH:16][CH:15]=1)[CH2:5][OH:6])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86652104HCID 86652104, compound

Product 1

HCID 58188209HCID 58188209, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (S)-5-(1-azido-2-(tert-butyldimethylsilyloxy)ethyl)-2-(difluoromethyl)pyridine (1.9 g, 5.79 mmol) in 20 mL of EtOH at 0° C. was added 5 mL 6N HCl and the resultant reaction mixture was slowly warmed to room temperature over a period of 2 h. The solvents were evaporated and the residue was separated between 10% NaHCO3 solution and CH2Cl2. The organic layer was dried over anhydrous Na2SO4 and the solvents were evaporated in vacuo to afford the title compound (1.1 g, 89% yield). MS: 215 [M+1]+; 1H-NMR (300 MHz, CDCl3): 8.63 (s, 1H), 7.86 (d, 1H, J=8.3 Hz), 7.68 (d, 1H, J=8.3 Hz), 6.65 (t, 1H, J=55.2 Hz), 4.75-4.79 (m 1H), 3.70-3.90 (m, 2H).

Workup

  1. customthe resultant reaction mixture
  2. customThe solvents were evaporated
  3. customthe residue was separated between 10% NaHCO3 solution and CH2Cl2
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-62553140c40d46048fee30076fdd6fd2
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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