Sodium borohydride → 7-(Hydroxymethyl)-4-azaspiro[2.4]heptan-5-one

HRID 595261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595261
[BH4-].[Na+].[O:3]=[C:4]1[CH2:10][CH:9]([CH:11]=[O:12])[C:6]2([CH2:8][CH2:7]2)[NH:5]1>CO.O>[OH:12][CH2:11][CH:9]1[C:6]2([CH2:8][CH2:7]2)[NH:5][C:4](=[O:3])[CH2:10]1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 916185615-Oxo-4-azaspiro[2.4]heptane-7-carbaldehyde

Produkt 1

HCID 916184147-(Hydroxymethyl)-4-azaspiro[2.4]heptan-5-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium borohydride (1.4 g, 6.6 mmol) was added to a stirred solution of 5-oxo-4-azaspiro[2.4]heptane-7-carbaldehyde (0.51 g, 3.3 mmol) in methanol (8 mL) and water (12 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was dried over sodium sulfate and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (1:10 methanol in dichloromethane, Rf=0.4) to give 7-(hydroxymethyl)-4-azaspiro[2.4]heptan-5-one. 1H NMR (400 MHz, CD3OD) δ 3.65-3.42 (m, 2H), 2.73-2.55 (m, 1H), 2.46-2.22 (m, 2H), 1.11-0.92 (m, 1H), 0.83-0.59 (m, 3H).

Aufarbeitung

  1. dry with materialThe reaction mixture was dried over sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customto afford the crude product residue
  4. customThe crude product residue was purified by silica gel chromatography (1:10 methanol in dichloromethane, Rf=0.4)

Quellen und Nachweise

ORD-Eintrag
ord-a153221c65cc478a8b9605a10055c552
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242984B2

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