Lithium borohydride → HCID 66895821, compound

HRID 337578Notes

Reaction equation

HRID 337578 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH2:23][CH2:24][C:25](OC)=[O:26])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:3][CH2:2]1.[BH4-].[Li+]>C1COCC1.CCOCC>[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH2:23][CH2:24][CH2:25][OH:26])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5](=[O:6])[O:7][C:8]([CH3:10])([CH3:11])[CH3:9])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 66896175HCID 66896175, compound

Product 1

HCID 66895821HCID 66895821, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-{8-[(cyclopropyl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-6-quinolinyl}propanoate (1 eq.) from the previous step in THF (0.08 M) was added lithium borohydride (5 eq.). The resulting mixture was stirred at RT for 14 h before it was diluted with ether and quenched with 1 N aq. NaOH. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a colorless oil.

Workup

  1. customquenched with 1 N aq. NaOH
  2. customThe aqueous layer was separated
  3. extractionback-extracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-abfd304f84de4b80a09ffaefd9ab7b01
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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