Lithium Hydroxide → HCID 66609262, compound

HRID 1529548Notes

Reaction equation

HRID 1529548 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 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

Alternatively, the compound A7 can be prepared by conventional heating. Briefly, lithium hydroxide (CAS: 1310-65-2; 7.6 g, 320 mmol) was added to a stirred solution of 6,7-dihydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (19.2 g, 63.7 mmol) in a mixture of H2O (70 mL) and 1,4-dioxane (200 mL) under N2. The mixture was stirred at 125° C. for 90 hours and filtered through a pad of diatomaceous earth. The pad was washed with water and AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by short open column chromatography (silica; 7N solution of ammonia in methanol in dichloromethane, 0/100 to 3/97). The desired fractions were collected and evaporated in vacuo to yield 4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine (6.4 g, 44% yield) as a brownish oil.

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. washThe pad was washed with water and AcOEt
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo
  7. customThe crude product was purified by short open column chromatography (silica; 7N solution of ammonia in methanol in dichloromethane, 0/100 to 3/97)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-fe442e21abec4a199315e7ddbf81d8cc
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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