Sodium borohydride → HCID 86633743, compound

HRID 415552Notes

Reaction equation

HRID 415552 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C@H:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)([O-])=O>CO.CO.ClCCl.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:3][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C@H:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

6

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86633744HCID 86633744, compound

Product 1

HCID 86633743HCID 86633743, compoundYield 93.7%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Sodium borohydride (110 mg, 2.8 mmol) was added to a solution of nickel (II) chloride hexahydrate (330 mg, 1.4 mmol) in 10 mL of methanol. A solution of benzyl (3R)-3-[(3-nitroquinolin-4-yl)amino]butylcarbamate (1.11 g, 2.81 mmol) in 20 mL of 1:1 methanol/dichloromethane was added, and the resulting dark mixture was stirred for 5 minutes at room temperature. Additional sodium borohydride was added in small portions until the reaction solution become colorless. The mixture was filtered through a layer of CELITE filter agent, and the filtrate was concentrated under reduced pressure. The resulting brown solid was triturated with dichloromethane, and the resulting mixture was filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure to provide 0.96 g of benzyl (3R)-3-[(3-aminoquinolin-4-yl)amino]butylcarbamate as a brown foam.

Workup

  1. filtrationThe mixture was filtered through a layer of CELITE filter agent
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting brown solid was triturated with dichloromethane
  4. filtrationthe resulting mixture was filtered through a layer of CELITE filter agent
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3df0586a16d44b379b47b31a6480d3df
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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