Sodium triacetoxyborohydride → HCID 67223794, compound

HRID 1968175Notes

Reaction equation

HRID 1968175 reaction equation
[CH:1]([C:3]1[C:11]2[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=2[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=1)=O.[NH2:23][C:24]1([CH3:37])[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:33]([O:32][C:30]([N:27]1[CH2:26][CH2:25][C:24]([NH:23][CH2:1][C:3]2[C:11]3[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=3[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=2)([CH3:37])[CH2:29][CH2:28]1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11310432tert-Butyl 4-amino-4-methylpiperidine-1-carboxylateHCID 58293521HCID 58293521, compound

Product 1

HCID 67223794HCID 67223794, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (71 mg, 0.233 mmol) was dissolved in DCM (5 mL) and tert-butyl 4-amino-4-methylpiperidine-1-carboxylate (50 mg, 0.233 mmol) was added to the solution and allowed to stir for 2 h at room temperature. Then sodium triacetoxyborohydride (148 mg, 0.700 mmol) was added and the mixture was allowed to stir for 2 h at room temperature. The solution was quenched with water and extracted with DCM. The organics were dried over MgSO4 and concentrated in vacuo. Purification by silica gel chromatography (70% EtOAc/Hexanes) gave 90 mg of 1-tert-butyl 4-methyl 3-((1-(tert-butoxycarbonyl)-4-methylpiperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate. [M+H] found 403.

Workup

  1. stirringto stir for 2 h at room temperature
  2. customThe solution was quenched with water
  3. extractionextracted with DCM
  4. dry with materialThe organics were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (70% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-56dec136b5ed422583353e1c8991f3ef
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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