Methanol → HCID 11845249, compound

HRID 1158870Notes

Reaction equation

HRID 1158870 reaction equation
[Li+].[BH4-].CO.C([O:7][C:8]([C:10]1[CH:18]=[C:13]2[CH2:14][S:15][CH2:16][CH2:17][N:12]2[N:11]=1)=O)C>C1COCC1>[N:11]1[N:12]2[C:13]([CH2:14][S:15][CH2:16][CH2:17]2)=[CH:18][C:10]=1[CH2:8][OH:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 11845093Ethyl 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazine-2-carboxylate

Product 1

HCID 11845249HCID 11845249, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

LiBH4 (cont. 90%) (536 mg) and MeOH (0.9 mL) was added to the THF (59 mL) solution of 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazine-2-carboxylic acid ethyl ester (3.13 g) under a nitrogen atmosphere at room temperature and stirred for 3 h at 40° C. The mixture was quenched with 1 mol/L HCl at pH 1 and stirred for 1 h at room temperature. Solid K2CO3 was added to the solution to adjust pH to 8 and the mixture was extracted with AcOEt. The organic layer was dried (K2CO3) and filtered. The filtrate was concentrated under reduced pressure to afford titled compound as pale yellow oil (2.51 g, quant.).

Workup

  1. customThe mixture was quenched with 1 mol/L HCl at pH 1
  2. stirringstirred for 1 h at room temperature
  3. additionSolid K2CO3 was added to the solution
  4. extractionthe mixture was extracted with AcOEt
  5. dry with materialThe organic layer was dried (K2CO3)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-af701bb449314341948a2a84fe2046a5
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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