Sodium triacetoxyborohydride → HCID 68993740, compound

HRID 657155Notes

Reaction equation

HRID 657155 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][NH:7][CH2:6][C@@H:5]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH2:4]1.[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]2[N:31]=[CH:30][C:29](=[O:32])[N:28]([CH2:33][CH:34]=O)[C:27]=2[N:36]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)(Cl)Cl>[CH3:1][O:2][CH:3]1[CH2:8][N:7]([CH2:34][CH2:33][N:28]2[C:29](=[O:32])[CH:30]=[N:31][C:26]3[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[N:36][C:27]2=3)[CH2:6][CH:5]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH2:4]1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 57815220(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehydeHCID 68991151HCID 68991151, compound

Product 1

HCID 68993740HCID 68993740, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To cis-2-{[(3RS,5SR)-5-(methyloxy)-3-piperidinyl]methyl}-1H-isoindole-1,3(2H)-dione (125 mg, 0.43 mmol) in MeOH (1 ml) and CHCl3 (5 ml) was added [6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]acetaldehyde (for a preparation see Example 126(e)) (100 mg; 0.50 mmol) and the reaction was allowed to stir at room temperature under N2 for 4 hours. Na(OAc)3BH (210 mg; 1.0 mmol) was added and the reaction was allowed to stir at room temperature under nitrogen for an additional 14 hours. The reaction was partitioned between saturated aqueous NaHCO3 (5 mL) and CH2Cl2 (20 mL), the aqueous layer was further extracted with CH2Cl2 (20 mL), and the combined organic layers were dried over Na2SO4. The solvents were removed and the crude residue was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient to provide the desired compound (10 mg; 55%) as a colorless oil.

Workup

  1. stirringto stir at room temperature under nitrogen for an additional 14 hours
  2. customThe reaction was partitioned between saturated aqueous NaHCO3 (5 mL) and CH2Cl2 (20 mL)
  3. extractionthe aqueous layer was further extracted with CH2Cl2 (20 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customThe solvents were removed
  6. customthe crude residue was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient

Sources & evidence

ORD record
ord-9961a5a0e1524a45af57b55729cd2f92
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

Loading…