Hydrochloric Acid → HCID 68680811, Verbindung

HRID 2245834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245834
[Si](O[CH2:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH:19]([O:22]C)OC)[C:13]1=[O:24])(C(C)(C)C)(C)C.Cl.[NH:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33](=[O:47])[NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:28][CH2:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(#N)C>[OH:22][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][N:12]([CH2:11][CH2:10][CH2:9][N:26]2[CH2:27][CH2:28][CH:29]([O:32][C:33](=[O:47])[NH:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:30][CH2:31]2)[C:13]1=[O:24]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl EsterHCID 68680479HCID 68680479, Verbindung

Produkt 1

HCID 68680811HCID 68680811, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To crude 1-[3-(tert-butyldimethylsilanyloxy)propyl]-3-(3,3-dimethoxypropyl)imidazolidin-2-one (11.4 g, 32 mmol; prepared as described in Preparation 2) was added to a 1:1 mixture of 1N aqueous HCl (32 mL, 32 mmol, 1.0 eq) in ACN (32 mL). The reaction was allowed to stir at room temperature for 2 hours. To the reaction mixture was added biphenyl-2-ylcarbamic acid piperidin-4-yl ester (9.4 g, 32 mmol; prepared as described in Preparation 3) and was allowed to stir for 30 minutes, followed by the addition of NaBH(OAc)3 (20.3 g, 96 mmol). The reaction mixture was allowed to stir overnight. After overnight, the solution was concentrated in vacuo. The crude mixture was taken up in DCM (400 mL) and washed with 1N NaOH (200 mL), water (200 mL) and brine (200 mL). The organic phase was dried over MgSO4, filtered and concentrated then purified via silica gel chromatography (10% MeOH in DCM with 1% NH3(aq)) to afford the title compound (7.98 g, 16.6 mmol) in 52% yield.

Aufarbeitung

  1. stirringto stir for 30 minutes
  2. stirringto stir overnight
  3. waitAfter overnight
  4. concentrationthe solution was concentrated in vacuo
  5. washwashed with 1N NaOH (200 mL), water (200 mL) and brine (200 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthen purified via silica gel chromatography (10% MeOH in DCM with 1% NH3(aq))

Quellen und Nachweise

ORD-Eintrag
ord-e8ec1a0755e648c2a5c656d1e2b0fd18
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683173B2

Notizen zur Reaktion

Wird geladen…