Potassium Carbonate → HCID 21979767, compound

HRID 1054020Notes

Reaction equation

HRID 1054020 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][CH:21](N)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>CC(O)=O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][CH:21]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]=[CH:7]3)[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 24436Sodium SulfateHCID 707665-AminoisoquinolineHCID 5458091-BOC-3-AminopiperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21979767HCID 21979767, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-amino-isoquinoline (47 g, 0.320 mol) in CH3COOH (1800 mL) was added 3-amino-piperidine-1-carboxylic acid tert-butyl ester (69.6 g, 0.376 mol) and Na2SO4 (267 g, 1.88 mol) at room temperature. The mixture was stirred at room temperature for 0.5 hour. Then to the mixture was added NaBH(OAc)3 (84.6 g, 0.376 mol) by portions. The mixture was stirred at room temperature for 18 hours. The mixture was adjusted to pH 8 by the addition of K2CO3 and extracted with EtOAc (2 L×3). The combined layers were dried over Na2SO4, filtered and then concentrated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=5:1) to give 3-(isoquinolin-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (55 g, 53%) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with EtOAc (2 L×3)
  3. dry with materialThe combined layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a0ef3d0904824beb83e0e6f0a4f3b4aa
Source dataset
uspto-grants-2016_07
Patent number
US09394286B2

Reaction notes

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