Reaktion #357724

Reaktionsgleichung

(1R,3S)-3-isopropyl-3-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)cyclopentanamine bis(trifluoroacetate)

tetrahydro-4H-pyran-4-one

triethylamine

sodium triacetoxyborohydride

→

N-[(1R,3S)-3-isopropyl-3-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)cyclopentyl]tetrahydro-2H-pyran-4-amine

Lösungsmittel

EtOAc

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with saturated Na2CO3
2. 2
   ExtraktionThe aqueous layer was extracted with EtOAc three times
3. 3
   TrocknenThe combined organic layers were dried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   Sonstigepurified on silica gel eluting with EtOAc to 1% Et3N/EtOAc providing 63 mg (84%) of the desired product, which
6. 6
   Sonstigewas further purified by HPLC
7. 7
   Sonstigeto give the product as diTFA salt

Vorschrift

To a solution of (1R,3S)-3-isopropyl-3-({4-[3-(trifluoromethyl)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.

Quelle