Lithium pyrrolidinoborohydride → 9-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)nonanoic acid

HRID 517897

Reaction equation

HRID 517897 reaction equation
O=[C:2]1[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=[C:5]2[CH2:4][CH2:3]1.N1([BH3-])CCCC1.[Li+]>C1COCC1>[C:14]1([CH3:17])[CH:13]=[CH:12][C:11]([C:9]2[N:10]=[C:5]3[CH2:4][CH2:3][CH2:2][N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:6]3=[N:7][C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 23697345Lithium pyrrolidinoborohydrideHCID 716576499-(6-Oxo-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)nonanoic acid

Product 1

HCID 896898969-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)nonanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9-(6-Oxo-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)nonanoic acid (Example 8) (200 mg, 0.412 mmol) in THF (10 ml) was stirred under N2 for 10 mins. Lithium pyrrolidinoborohydride (1M in THF) (2.059 ml, 2.059 mmol) was added carefully and the resulting mixture was stirred at RT for 1.5 hours. The reaction was quenched with 1M HCl and the mixture was concentrated under reduced pressure. The resulting mixture was extracted with DCM and the organic extracts were passed through a phase separating column. The organics were concentrated under reduced pressure and purification of the crude product by chromatography on silica eluting with 0-100% EtOAc in iso-hexane afforded the titled compound;

Workup

  1. customThe reaction was quenched with 1M HCl
  2. concentrationthe mixture was concentrated under reduced pressure
  3. extractionThe resulting mixture was extracted with DCM
  4. customseparating column
  5. concentrationThe organics were concentrated under reduced pressure and purification of the crude product by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-52b9509e4b13464eba5333f3799fc174
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Linked notes

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