Ammonium Acetate → Methyl 6-aminospiro[4.5]decane-7-carboxylate

HRID 539931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539931
O=[C:2]1[CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][CH2:9][CH2:8][C:3]21[CH2:7][CH2:6][CH2:5][CH2:4]2.C([O-])(=O)C.[NH4+].[BH3-]C#[N:23].[Na+]>CO>[NH2:23][CH:2]1[CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][CH2:9][CH2:8][C:3]21[CH2:7][CH2:6][CH2:5][CH2:4]2

Komponenten

5

Edukt 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57429459Methyl 6-oxospiro[4.5]decane-7-carboxylate

Produkt 1

HCID 67973872Methyl 6-aminospiro[4.5]decane-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In a flask containing methyl 6-oxospiro[4.5]decane-7-carboxylate, 60, (4.10 g, 19.50 mmol) in MeOH (35 mL) was added ammonium acetate (10.52 g, 136.50 mmol) and NaCNBH3 (1.47 g, 23.40 mmol). The mixture was stirred at room temperature for 24 hrs. GCMS showed conversion to product SM (Rt=12.3 min, E+=211), product (Rt=12.6 min, ES+=212 [major] and Rt=12.45 min, ES+=212 [minor]). The solvent was evaporated, HCl (1N) was added and the aqueous phase was extracted with EtOAc. The organic phase was neutralized with NaOH (6N) to pH ˜10. The aqueous phase was extracted three times with EtOAc and twice with dichloromethane, dried over Na2SO4 to yield 1.6 g of product.

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionHCl (1N) was added
  3. extractionthe aqueous phase was extracted with EtOAc
  4. extractionThe aqueous phase was extracted three times with EtOAc
  5. dry with materialtwice with dichloromethane, dried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-c164d8df0f2949c181db85828fbd27ad
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871774B2

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