Methanol → Pyrazolo[5,1-b]oxazole-6-methanol, 2,3-dihydro-

HRID 2216618Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:13]=[C:9]2[O:10][CH2:11][CH2:12][N:8]2[N:7]=1)=O)C.[BH4-].[Li+].CO>C1COCC1>[O:10]1[CH2:11][CH2:12][N:8]2[N:7]=[C:6]([CH2:4][OH:3])[CH:13]=[C:9]12

Participants

Conditions

Temperature: 40 °C

Procedure

To the stirred solution of ethyl2,3-dihydropyrazolo[5,1-b][1,3]oxazole-6-carboxylate (5.47 g, 35 mmol) of in 100 ml of THF was added 1.05 g of lithium borohydride and 1.54 g of methanol. The solution was heated at 40° C. for 2.5 hour. The reaction was quenched by 1N HCl, and adjusted to pH 1.3 and stirred at room temperature for 1 hour. The reaction mixture was adjusted pH to 8 with k2CO3. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, and concentrated to an oil and column chromatographyed to give 2.68 g of the desired product (65%).

Workup

customThe reaction was quenched by 1N HCl
extractionThe reaction mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated to an oil and column

Sources & evidence

ORD record: ord-f2376497c33d49979401aa8f1efedffb
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112582B2

Reaction notes

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