Water → HCID 118020440, compound

HRID 1777375Notes

Reaction equation

HRID 1777375 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:21]2[N:25]=[CH:24][CH:23]=[N:22]2)=[C:6]([CH:20]=1)[C:7]([N:9]1[CH2:14][CH2:13][CH2:12][O:11][CH:10]1[C:15](OCC)=[O:16])=[O:8].[Li+].[BH4-].O>C1COCC1>[OH:16][CH2:15][CH:10]1[N:9]([C:7]([C:6]2[CH:20]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N:21]2[N:25]=[CH:24][CH:23]=[N:22]2)=[O:8])[CH2:14][CH2:13][CH2:12][O:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 118201023HCID 118201023, compound

Product 1

HCID 118020440HCID 118020440, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (±)-ethyl 3-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]-1,3-oxazinane-2-carboxylate obtained in Reference Example 3 (0.50 g, 1.5 mmol) in THF (5 mL), a solution of LiBH4 in THF (0.97 mL, 2.9 mmol) was added and stirred for 2 hours at room temperature. Water was added to the reaction mixture, followed by extraction with CHCl3. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over Na2SO4, then the drying agent was filtered off, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (HP-Sil 25 g, hexane/EtOAc=88/12 to 0/100) to obtain the title compound (0.34 g) (colorless oil).

Workup

  1. extractionfollowed by extraction with CHCl3
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over Na2SO4
  4. filtrationthe drying agent was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by column chromatography (HP-Sil 25 g, hexane/EtOAc=88/12 to 0/100)

Sources & evidence

ORD record
ord-e8cf2fa105624e67adf7701e9cbcaffa
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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