Ammonium Acetate → 4-Amino-1-[2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexanol

HRID 1354214Notes

Reaction equation

HRID 1354214 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:15][C:16]1([CH2:23][CH2:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[N:33]=3)[N:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C([O-])(=O)C.[NH4+:41]>CO.[NH4+].[OH-]>[NH2:41][CH:19]1[CH2:20][CH2:21][C:16]([CH2:23][CH2:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[N:33]=3)[N:28]=[CH:27][CH:26]=2)([OH:15])[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5049666Sodium triacetoxyborohydride2×HCID 211046474-Hydroxy-4-[2-(6-methoxy-[1,5]naphthyridin-4-yl)ethyl]-cyclohexanone

Product 1

HCID 218737274-Amino-1-[2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

Sodium triacetoxyborohydride (1.89 g, 8.75 mmol) was added to a solution of 4-hydroxy-4-[2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-cyclohexanone (3 g, 8.5 mmol) and ammonium acetate (25.5 g) in methanol (65 ml). The reaction mixture was stirred at room temperature for 3 hours, 0.5 g of sodium triacetoxyborohydride was added and stirring was continued for a further 2 hours. The reaction mixture was diluted with NH4OH and extracted with EtOAc and dichloromethane. Organic phases were dried over MgSO4 and concentrated.

Workup

  1. stirringstirring
  2. waitwas continued for a further 2 hours
  3. extractionextracted with EtOAc and dichloromethane
  4. dry with materialOrganic phases were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e768bbfef4274ad290c173fa4bb26f89
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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