Triethylamine → HCID 57938714, compound

HRID 1436755Notes

Reaction equation

HRID 1436755 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[CH:15]([C@:18]1([C:24]([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=3)[CH2:28][CH2:27]2)=[O:25])[CH2:22][CH2:21][C@@H:20]([NH2:23])[CH2:19]1)([CH3:17])[CH3:16].[CH3:42][O:43][CH:44]1[C:49](=O)[CH2:48][CH2:47][O:46][CH2:45]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:15]([C@:18]1([C:24]([N:26]2[CH2:31][CH2:30][N:29]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:41])[F:39])[CH:33]=3)[CH2:28][CH2:27]2)=[O:25])[CH2:22][CH2:21][C@@H:20]([NH:23][CH:49]2[CH2:48][CH2:47][O:46][CH2:45][CH:44]2[O:43][CH3:42])[CH2:19]1)([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 235336103-Methoxyoxan-4-oneHCID 86633368HCID 86633368, compound

Product 1

HCID 57938714HCID 57938714, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,3S)-3-isopropyl-3-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)cyclopentanamine bis(trifluoroacetate) (140 mg, 0.23 mmol), 3-methoxytetrahydro-4H-pyran-4-one (90 mg, 0.69 mmol) and triethylamine (0.096 mL, 0.69 mmol) in methylene chloride (10 mL) was added sodium triacetoxyborohydride (97 mg, 0.46 mmol). After being stirred at room temperature overnight, the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried (MgSO4), concentrated and purified on silica gel eluting with EtOAc to 1% Et3N/EtOAc affording 105 mg (92%) of the desired product. The product was separated by chiral HPLC to give two major isomers. MS calculated for C26H38F3N3O3: (M+H) 498; found 498.2 for both isomers.

Workup

  1. washwashed with saturated Na2CO3
  2. extractionThe aqueous layer was extracted with EtOAc three times
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified on silica gel eluting with EtOAc to 1% Et3N/EtOAc affording 105 mg (92%) of the desired product
  6. customThe product was separated by chiral HPLC
  7. customto give two major isomers

Sources & evidence

ORD record
ord-c08fe81c298b4bc981ae0a30416333e0
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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