Lithium borohydride → HCID 66896547, compound

HRID 337604Notes

Reaction equation

HRID 337604 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([C:17](OC)=[O:18])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:3])[CH3:2].[BH4-].[Li+]>C1COCC1.CCOCC>[OH:18][CH2:17][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:8]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 66896145HCID 66896145, compound

Product 1

HCID 66896547HCID 66896547, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-[2-(acetylamino)ethyl]-naphthalenecarboxylate (1 eq.) from the previous step was taken up in THF (0.18 M). To this solution was then added lithium borohydride (12 eq.) and the resulting solution was vigorously stirred at 50° C. for 5 h. The reaction mixture thus obtained was diluted further with ether and carefully quenched with 1 N aq. HCl. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. customThe reaction mixture thus obtained
  2. customcarefully quenched with 1 N aq. HCl
  3. customThe aqueous layer was separated
  4. extractionback-extracted with EtOAc
  5. washThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-37ffb167a9cd4cc8aadbe92f0e56a845
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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