Lithium borohydride → HCID 69060577, compound

HRID 1436889Notes

Reaction equation

HRID 1436889 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[CH2:5][N:6]1[CH2:11][CH2:10][C:9]([C:12](OC)=[O:13])=[CH:8][C:7]1=[O:16].[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[CH2:5][N:6]1[CH2:11][CH2:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]1=[O:16]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69067967HCID 69067967, compound

Product 1

HCID 69060577HCID 69060577, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 1-(3-chloro-4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-one-4-carboxylate (4.0 g, 13 mmol) from the previous step in THF (75 mL) was cooled to −78° C. with stirring. A solution of lithium borohydride in THF (15 mL of a 2.0 M solution, 30 mmol) was added and the mixture was stirred at −78° C. for 30 min and then at ambient temperature for 24 hours. The reaction was quenched by the careful addition of 1 N aqueous HCl. Enough HCl was added so that the solution measured pH 1. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 (100 mL) and water (50 mL). The organic layer was separated and the aqueous phase was extracted with more CH2Cl2 (2×100 mL). The organic phases were combined and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography eluting with 95:5 CH2Cl2:MeOH. Fractions containing product were concentrated under reduced pressure to give the title compound as a gum. HPLC RT=2.67 min (Method A); ES MS M+1=272.

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 min
  2. customThe reaction was quenched by the careful addition of 1 N aqueous HCl
  3. additionEnough HCl was added so that the solution
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between CH2Cl2 (100 mL) and water (50 mL)
  6. customThe organic layer was separated
  7. extractionthe aqueous phase was extracted with more CH2Cl2 (2×100 mL)
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by pressurized silica gel column chromatography
  10. washeluting with 95:5 CH2Cl2
  11. additionFractions containing product
  12. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-db4391b8ef6241ee8902f9dbf05f5110
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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