Lithium Hydroxide → HCID 66609262, compound

HRID 1529547Notes

Reaction equation

HRID 1529547 reaction equation
[OH-].[Li+].C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16][C:10]=2[CH2:9]1)=O)C>O.O1CCOCC1>[O:18]([CH2:17][C:15]1[O:16][C:10]2[CH2:9][NH:8][CH2:13][CH2:12][C:11]=2[N:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66609159HCID 66609159, compound

Product 1

HCID 66609262HCID 66609262, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
170 °C

Procedure

Lithium hydroxide (0.66 g, 27.7 mmol) was added to a stirred solution of 6,7-dihydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.77 g, 5.55 mmol) in a mixture of H2O (5 mL) and 1,4-dioxane (15 mL) under N2. The mixture was stirred at 170° C. for 40 minutes under microwave irradiation, diluted with H2O and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine (0.58 g, 45% yield) as a purple oil that was used in the next step without further purification. C13H14N2O2 LCMS: Rt 1.07, m/z 231 [M+H]+ (using method, LC-MS Method 6).

Workup

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

Sources & evidence

ORD record
ord-50c95e5fcbbb40319520a0bd04e6e757
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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