Lithium borohydride → HCID 135543046, compound

HRID 1767390Notes

Reaction equation

HRID 1767390 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[OH:30])[N:21]=[C:20]3[C:15]=2[CH:16]=[C:17]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:18](=[O:31])[NH:19]3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[OH:30])[N:21]=[C:20]3[C:15]=2[CH2:16][CH:17]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:18](=[O:31])[NH:19]3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 135528464HCID 135528464, compound

Product 1

HCID 135543046HCID 135543046, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) suspension of ethyl 5-[1-(tert-butoxycarbonyl)-3-piperidinyl]-7-(2-hydroxyphenyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate (0.050 g, 0.101 mmol) in THF (2.0 mL) under an argon atmosphere was added LiBH4 (0.004 g, 0.20 mmol). The mixture was allowed to warm to room temperature, and the stirring was continued for 3 hrs. The resulting mixture was quenched with water, and partitioned between ethyl acetate and a saturated ammonium chloride solution. The separated organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate, 3:2) to give Ethyl 5-[1-(tert-butoxycarbonyl)-3-piperidinyl]-7-(2-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate. (0.027 g, yield; 54%)

Workup

  1. customThe resulting mixture was quenched with water
  2. custompartitioned between ethyl acetate
  3. washThe separated organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate, 3:2)

Sources & evidence

ORD record
ord-f381a6cd220e47fca57807077a6e1957
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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