Lithium borohydride → HCID 86715103, compound

HRID 533912Notes

Reaction equation

HRID 533912 reaction equation
[O:1]=[C:2]1[C@H:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[S:15][C:16]([C:19](OC)=[O:20])=[CH:17][N:18]=3)=[N:12][CH:13]=2)[CH2:5][CH2:4][NH:3]1.[Li+].[BH4-]>C1COCC1>[OH:20][CH2:19][C:16]1[S:15][C:14]([C:11]2[N:12]=[CH:13][C:8]([O:7][C@@H:6]3[CH2:5][CH2:4][NH:3][C:2]3=[O:1])=[CH:9][CH:10]=2)=[N:18][CH:17]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86715104HCID 86715104, compound

Product 1

HCID 86715103HCID 86715103, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 2-(5-(2-oxopyrrolidin-3-yloxy)pyridin-2-yl)thiazole-5-carboxylate (360 mg) in THF (5 mL) was added LiBH4 (100 mg) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 12 hours. After cooling to 0° C., the reaction was quenched by dropwise addition of water (until no more gas was generated). The reaction mixture was diluted with ethyl acetate (50 mL). The organic layer was washed with water (30 mL×2) and brine (20 mL) and dried over anhydrous Na2SO4. After filtration and evaporation of the solvent, the residue obtained was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (4:1 to pure EA) to afford the title compound. MS ESI+: m/z=292 [M+H]+.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe reaction was quenched by dropwise addition of water (until no more gas
  3. additionThe reaction mixture was diluted with ethyl acetate (50 mL)
  4. washThe organic layer was washed with water (30 mL×2) and brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration and evaporation of the solvent
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography
  9. washeluting with petroleum ether/ethyl acetate (4:1 to pure EA)

Sources & evidence

ORD record
ord-3977f8281a5149509d0adf9c4b6b194c
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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