Sodium Nitrite → (S)-1-(6-Benzyloxyindazol-1-yl)-propan-2-ol

HRID 2121868

Reaktionsgleichung

Reaktionsgleichung von HRID 2121868
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([NH:17][CH2:18][C@@H:19]([OH:21])[CH3:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]([O-])=O.[Na+]>C(O)(=O)C.O.[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([CH:13]=[N:22][N:17]2[CH2:18][C@@H:19]([OH:21])[CH3:20])=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 23668193Sodium NitriteHCID 867596484-Benzyloxy-2-((S)-2-hydroxy-propylamino)-benzaldehyde

Produkt 1

HCID 11659201(S)-1-(6-Benzyloxyindazol-1-yl)-propan-2-olAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 21899381Acetic acid--water (1/1)Lösungsmittel

Versuchsvorschrift

To a mixture of the product from Step C (16.0 g, 56.1 mmol) in acetic acid/water (150 mL/30 mL) at 0° C. was added sodium nitrite (7.75 g, 112 mmol) in portions over 40 min. The mixture was stirred for 50 min, cooled (ice bath), and zinc (14.7 g, 224 mmol) was added in portions. After 1 h the suspension was warmed to room temperature and more zinc was added (14.7 g, 224 mmol). The mixture was stirred for 1 h, concentrated, and extracted with EtOAc (2×300 mL). The extracts were filtered through a filter-aide, and the filtrate was washed with saturated aqueous disodium hydrogen phosphate (to pH 8) and brine, dried, and purifed by chromatrography (silica, 25% EtOAc/hexane) to afford an oil (7.01 g, 44%).

Aufarbeitung

  1. additionwas added in portions
  2. stirringThe mixture was stirred for 1 h
  3. concentrationconcentrated
  4. extractionextracted with EtOAc (2×300 mL)
  5. filtrationThe extracts were filtered through a filter-aide
  6. washthe filtrate was washed with saturated aqueous disodium hydrogen phosphate (to pH 8) and brine
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-856ec49db9e04f109edccd1f32a87a20
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696476B2

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