Sodium borohydride → HCID 178479966, Verbindung

HRID 511244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511244
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2.[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:13]2[CH2:18][CH2:17][C@@H:16]([OH:19])[CH2:15][CH2:14]2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 672561257-amino-2-methyl-4-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindol-1-one

Produkt 1

HCID 178479966HCID 178479966, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 7-amino-2-methyl-4-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindol-1-one (1.35 g, 5.23 mmol) was dissolved in MeOH (30 mL), and cooled to 0° C., followed by addition of sodium borohydride (0.198 g, 5.23 mmol). The reaction mixture was stirred at 0° C. for 1 h. The reaction was quenched with sat. aq. NH4Cl, diluted with EtOAc, washed with brine, and dried over anhydrous sodium sulfate. The compound was purified on an Isco Combiflash eluting with 0 to 4% MeOH in EtOAc to afford the trans isomer and the cis isomer. Trans-isomer: 1H NMR (400 MHz, DMSO-d6) δ 7.05 (d, J=8.34 Hz, 1H), 6.51 (d, J=8.34 Hz, 1H), 5.83 (s, 2H), 4.53 (d, J=4.29 Hz, 1H), 4.33 (s, 2H), 3.38-3.48 (m, 1H), 2.98 (s, 3H), 2.28-2.38 (m, 1H), 1.90 (d, J=9.35 Hz, 2H), 1.68 (d, J=12.38 Hz, 2H), 1.38-1.51 (m, 2H), 1.19-1.32 (m, 2H); MS (ES+): m/z: 262.1674 [MH+]. HPLC: tR=0.98 min (UPLC TOF MS: polar—3 min). Cis-isomer: 1H NMR (400 MHz, DMSO-d6) δ 7.07 (d, J=8.34 Hz, 1H), 6.54 (d, J=8.34 Hz, 1H), 5.83 (s, 2H), 4.33 (s, 3H), 2.99 (s, 3H), 2.34-2.43 (m, 1H), 1.70-1.87 (m, 4H), 1.38-1.57 (m, 4H); MS (ES+): m/z: 262.1693 [MH+]. HPLC: tR=1.04 min (UPLC TOF MS: polar—3 min).

Aufarbeitung

  1. customThe reaction was quenched with sat. aq. NH4Cl
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe compound was purified on an Isco Combiflash
  6. washeluting with 0 to 4% MeOH in EtOAc
  7. customto afford the trans isomer
  8. customHPLC: tR=0.98 min (UPLC TOF MS: polar—3 min)
  9. customHPLC: tR=1.04 min (UPLC TOF MS: polar—3 min)

Quellen und Nachweise

ORD-Eintrag
ord-d249c05f49a5472fa01eafe13c59ec57
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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