Trifluoroacetic acid → 4,5,6,7-Tetrahydro-2-(phenoxymethyl)-oxazolo[4,5-c]pyridine

HRID 1529561Notes

Reaction equation

HRID 1529561 reaction equation
FC(F)(F)C(O)=O.CC(OC([N:15]1[CH2:20][CH2:19][C:18]2[O:21][C:22]([CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:23][C:17]=2[CH2:16]1)=O)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[O:25]([CH2:24][C:22]1[O:21][C:18]2[CH2:19][CH2:20][NH:15][CH2:16][C:17]=2[N:23]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 666088866,7-dihydro-2-(phenoxymethyl)-oxazolo[4,5-c]pyridine-5(4H)-carboxylic acid 1,1-dimethylethyl ester

Product 1

HCID 666090124,5,6,7-Tetrahydro-2-(phenoxymethyl)-oxazolo[4,5-c]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.0 mL, 13.0 mmol) was added to a solution of 6,7-dihydro-2-(phenoxymethyl)-oxazolo[4,5-c]pyridine-5(4H)-carboxylic acid 1,1-dimethylethyl ester (0.11 g, 0.35 mmol) in DCM (1 mL). The mixture was stirred at room temperature for 30 minutes and basified with a saturated solution of Na2CO3. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[4,5-c]pyridine (80 mg, 100% yield, 30% pure) that was used in the next step without further purification. C13H14N2O2 LCMS: Rt 0.65, m/z 231 [M+H]+ (using method, LC-MS Method 7).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-c9d6afcfbebe410e800a0a833744f23b
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

Loading…