Triethylamine → Ammonium hydroxide methanol

HRID 1044570Notes

Reaction equation

HRID 1044570 reaction equation
Cl.[CH:2]([C@:5]1([C:11]([N:13]2[CH2:18][CH:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[CH2:9][CH2:8][C@@H:7]([NH2:10])[CH2:6]1)([CH3:4])[CH3:3].C[O:26][CH:27]1[C:32](=O)[CH2:31][CH2:30][O:29][CH2:28]1.C([N:36](CC)CC)C.[C:41](O[BH-](OC(=O)C)OC(=O)C)(=[O:43])C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH4+:10].[OH-:12].[NH4+:36].[OH-:26].[CH3:41][OH:43].[CH:2]([C@:5]1([C:11]([N:13]2[CH2:14][CH:15]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:9][CH2:8][C@@H:7]([NH:10][CH:32]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:6]1)([CH3:4])[CH3:3]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 235336103-Methoxyoxan-4-oneHCID 68599587HCID 68599587, compound

Product 3

HCID 14923Ammonium HydroxideHCID 11567437HCID 11567437, compoundHCID 21894508Ammonium hydroxide methanolYield 1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,3S)-3-isopropyl-3-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]cyclopentanamine hydrochloride (50 mg, 0.1 mmol), 3-methoxytetrahydro-4H-pyran-4-one (56 mg, 0.43 mmol), and triethylamine (0.07 mL, 0.5 mmol) in methylene chloride (2 mL) was added sodium triacetoxyborohydride (91 mg, 0.43 mmol). After being stirred at room temperature overnight, saturated NaHCO3 was added. The solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (gradient 0-15% B over 15 min. Bottle A=1% NH4OH/3% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) afforded the desired compound. MS calculated for C26H35N2O3: (M+H) 427; found 427.3.

Workup

  1. extractionThe solution was extracted with methylene chloride three times
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel (gradient 0-15% B over 15 min

Sources & evidence

ORD record
ord-ff5352a042c04a9b9c59c32de947f5a6
Source dataset
uspto-grants-2013_10
Patent number
US08563582B2

Reaction notes

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