Lithium borohydride → HCID 131732038, compound

HRID 337689Notes

Reaction equation

HRID 337689 reaction equation
[CH:1]1([N:4]([CH2:28][C:29]2[CH:34]=[C:33]([CH2:35][CH2:36][CH2:37][C:38](OC)=[O:39])[CH:32]=[C:31]([Cl:42])[C:30]=2[Cl:43])[C:5]([C@H:7]2[C@H:12]([C:13]3[CH:18]=[CH:17][N:16]([CH3:19])[C:15](=[O:20])[CH:14]=3)[CH2:11][CH2:10][N:9]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:8]2)=[O:6])[CH2:3][CH2:2]1.[BH4-].[Li+]>C1COCC1>[CH:1]1([N:4]([CH2:28][C:29]2[CH:34]=[C:33]([CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[CH:32]=[C:31]([Cl:42])[C:30]=2[Cl:43])[C:5]([C@H:7]2[C@H:12]([C:13]3[CH:18]=[CH:17][N:16]([CH3:19])[C:15](=[O:20])[CH:14]=3)[CH2:11][CH2:10][N:9]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:8]2)=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 131732039HCID 131732039, compound

Product 1

HCID 131732038HCID 131732038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution (0.08 M) of trans-1,1-dimethylethyl 3-{[cyclopropyl({2,3-dichloro-5-[4-(methyloxy)-4-oxobutyl]phenyl}methyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-1-piperidinecarboxylate (1 eq.) from the previous step was added lithium borohydride (6 eq.) in one rapid portion. After 3 h, the reaction was quenched with the careful addition of 10% aq. HCl. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extract 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 froth.

Workup

  1. customthe reaction was quenched with the careful addition of 10% aq. HCl
  2. customThe aqueous layer was separated
  3. extractionback-extracted with EtOAc
  4. extractionThe combined organic extract
  5. washwere washed further with 1 N aq. NaOH, water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-87f759b37ae44767a665217fd35472b2
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…