Diisopropylethylamine → HCID 178468169, Verbindung

HRID 2060059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060059
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](=[O:11])[N:8]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:7]=2[CH:18]=1.[CH2:19]([O:21][CH:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)[CH3:20].CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1CCCC1=O.CO>[CH2:19]([O:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([N:15]2[CH2:14][CH2:13][CH:12]([N:8]3[C:7]4[CH:18]=[C:3]([F:2])[CH:4]=[CH:5][C:6]=4[O:10][C:9]3=[O:11])[CH2:17][CH2:16]2)[CH2:24][CH2:23]1)[CH3:20]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 5464704-Ethoxycyclohexan-1-oneHCID 5049666Sodium triacetoxyborohydrideHCID 68479981HCID 68479981, Verbindung

Produkt 1

HCID 178468169HCID 178468169, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of 5-fluoro-3-(4-piperidinyl)-1,3-benzoxazol-2(3H)-one hydrochloride D138 (0.2 g), 4-(ethyloxy)cyclohexanone (WO2007107566) (0.2 g), and Hunig's base (0.1 g) in N-methylpyrrolidone (5 mL) was stirred for 2 hours then treated with sodium triacetoxyborohydride (0.5 g) was added and stirring was continued for four days. The mixture was diluted with methanol, loaded onto a SCX column and the column was eluted with methanol followed by 2M ammonia in methanol. The methanolic ammonia fractions were evaporated and the residue was purified by high pH MDAP. Two peaks were collected and evaporated separately. The fast eluting isomer gave 3-{1-[trans-4-(ethyloxy)cyclohexyl]-4-piperidinyl}-5-fluoro-1,3-benzoxazol-2(3H)-one E52 as a white solid (7 mg).

Aufarbeitung

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for four days
  4. washthe column was eluted with methanol
  5. customThe methanolic ammonia fractions were evaporated
  6. customthe residue was purified by high pH MDAP
  7. customTwo peaks were collected
  8. customevaporated separately

Quellen und Nachweise

ORD-Eintrag
ord-243fe2e4b9244f8ba5a032a372d51445
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278328B2

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