Triethylamine → Ammonium hydroxide methanol

HRID 270564Notes

Reaction equation

HRID 270564 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][C:20]=3[C:25]([F:28])([F:27])[F:26])[CH2:15][CH2:14]2)=[O:12])[CH2:9][CH2:8][C@@H:7]([NH2:10])[CH2:6]1)([CH3:4])[CH3:3].[O:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.C([N:38](CC)CC)C.[C:43](O[BH-](OC(=O)C)OC(=O)C)(=[O:45])C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH4+:10].[OH-:12].[NH4+:38].[OH-:29].[CH3:43][OH:45].[CH:2]([C@:5]1([C:11]([N:13]2[CH2:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:26])[F:27])[CH2:17][CH2:18]2)=[O:12])[CH2:9][CH2:8][C@@H:7]([NH:10][CH:32]2[CH2:33][CH2:34][O:29][CH2:30][CH2:31]2)[CH2:6]1)([CH3:4])[CH3:3]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68595386HCID 68595386, compound

Product 3

HCID 14923Ammonium HydroxideHCID 11719634HCID 11719634, compoundHCID 21894508Ammonium hydroxide methanolYield 1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,3S)-3-isopropyl-3-{[4-[2-(trifluoromethyl)phenyl]-3,6-dihydropyridin-1(2H)-yl]carbonyl}cyclopentanamine hydrochloride (46 mg, 0.11 mmol), tetrahydro-4H-pyran-4-one (33 mg, 0.33 mmol), and triethylamine (0.054 mL, 0.39 mmol) in methylene chloride (2 mL) was added sodium triacetoxyborohydride (70 mg, 0.33 mmol). After being stirred overnight at room temperature, a saturated NaHCO3 solution was added. The resulting solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (0-20% B over 15 min. Bottle A=1% NH4OH/2% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) provided the desired product. MS calculated for C26H35F3N2O2: (M+H) 465; found 465.2.

Workup

  1. extractionThe resulting 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 (0-20% B over 15 min

Sources & evidence

ORD record
ord-33b3ed93a84d4e1cbb510210aa49293c
Source dataset
uspto-grants-2008_11
Patent number
US07449467B2

Reaction notes

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