Potassium Carbonate → HCID 21979767, compound

HRID 1520235Notes

Reaction equation

HRID 1520235 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 temperate for 0.5 hour. Then to the mixture was added NaBH(OAc)3 (84.6 g, 0.376 mol) little by little. 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 in vacuo to afford crude product, which 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 material(The combined layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford crude product, which
  7. customwas purified by column chromatography on silica gel (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-4bcb365da51645a594ccfb2dbe146390
Source dataset
uspto-grants-2015_07
Patent number
US09073905B2

Reaction notes

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