Triethylamine → HCID 11669935, compound

HRID 1261638Notes

Reaction equation

HRID 1261638 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](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]=C[CH:35]=[C:34](CC(F)(F)F)[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].[O:43]1[CH2:48][CH2:47][C:46](=O)[CH2:45][CH2:44]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:33]=[CH:34][CH:35]=[C:3]([C:2]([F:7])([F:6])[F:1])[CH:37]=3)[CH2:28][CH2:27]2)=[O:25])[CH2:22][CH2:21][C@@H:20]([NH:23][CH:46]2[CH2:47][CH2:48][O:43][CH2:44][CH2:45]2)[CH2:19]1)([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 86641535HCID 86641535, compound

Product 1

HCID 11669935HCID 11669935, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,3S)-3-isopropyl-3-({4-[3-(trifluoro ethyl)phenyl]piperazin-1-yl}carbonyl)cyclopentanamine bis(trifluoroacetate) (98 mg, 0.16 mmol), tetrahydro-4H-pyran-4-one (0.044 mL, 0.48 mmol) and triethylamine (0.067 mL, 0.48 mmol) in methylene chloride (5 mL) was added sodium triacetoxyborohydride (68 mg, 0.32 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 providing 63 mg (84%) of the desired product, which was further purified by HPLC to give the product as diTFA salt. MS calculated for C25H36F3N3O2: (M+H) 468; found 468.2.

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 providing 63 mg (84%) of the desired product, which
  6. customwas further purified by HPLC
  7. customto give the product as diTFA salt

Sources & evidence

ORD record
ord-54d61e4b4630471ca87430202ab1e94f
Source dataset
uspto-grants-2013_06
Patent number
US08470827B2

Reaction notes

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