Sodium borohydride → HCID 90046925, Verbindung

HRID 1504997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504997
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][C:20](=[O:22])[CH3:21])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.C(Cl)Cl>[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH:20]([OH:22])[CH3:21])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:6])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 90046976HCID 90046976, Verbindung

Produkt 1

HCID 90046925HCID 90046925, VerbindungAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)propan-2-one (100 mg, 0.281 mmol) in MeOH (2810 μl) was added NaBH4 (13.29 mg, 0.351 mmol) at rt. This was stirred at rt for 20 min. Removed solvent in vacuo. Redissolved in DCM and quenched with sat aq NH4Cl. Separated and extracted twice more with DCM. Washed combined organics with brine, then dried on MgSO4, filtered and concentrated providing 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)propan-2-ol (98.8 mg, 0.276 mmol, 98% yield) as an off-white foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (d, J=6.06 Hz, 3H) 1.33 (s, 9H) 4.00-4.20 (m, 3H) 4.81 (d, J=4.29 Hz, 1H) 7.74 (s, 1H) 7.76 (d, J=4.80 Hz, 1H) 8.65 (s, 1H) 8.94 (d, J=4.80 Hz, 1H). MS: m/z: 358.1 [M+H]+.

Aufarbeitung

  1. customquenched with sat aq NH4Cl
  2. customSeparated
  3. extractionextracted twice more with DCM
  4. washWashed
  5. customdried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c928694d22ac49b184c82ab3e5c329d5
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216965B2

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