Triethylamine → Ammonium hydroxide methanol

HRID 270557Notes

Reaction equation

HRID 270557 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].[O:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH4+:10].[OH-:12].[CH3:26][OH:25].[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:28]2[CH2:29][CH2:30][O:25][CH2:26][CH2:27]2)[CH2:6]1)([CH3:4])[CH3:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68599587HCID 68599587, compound

Product 2

HCID 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), tetrahydro-4H-pyran-4-one (43 mg, 0.43 mmol), and triethylamine (0.070 mL, 0.50 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% NH40H/3% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) afforded the desired compound. MS calculated for C25H36N2O2: (M+H) 397; found 397.2.

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
  6. wait0-15% B over 15 min

Sources & evidence

ORD record
ord-878b34883570433d8c9da80eb5dfc432
Source dataset
uspto-grants-2008_11
Patent number
US07449467B2

Reaction notes

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