Isobutyraldehyde → 7-(2-Chlorophenyl)-1-isobutyl-1,7-diazaspiro[4.4]nonan-6-one

HRID 1672378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672378
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:16][CH2:15][C:10]2([NH:14][CH2:13][CH2:12][CH2:11]2)[C:9]1=[O:17].[CH:18](=O)[CH:19]([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:16][CH2:15][C:10]2([N:14]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12][CH2:11]2)[C:9]1=[O:17]

Komponenten

5

Edukt 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 589483317-(2-Chlorophenyl)-1,7-diazaspiro[4.4]nonan-6-one

Produkt 1

HCID 166550297-(2-Chlorophenyl)-1-isobutyl-1,7-diazaspiro[4.4]nonan-6-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

7-(2-Chlorophenyl)-1,7-diazaspiro[4.4]nonan-6-one (20 mg, 0.00008 mol) was dissolved in anhydrous DCM (2 mL). To this mixture was added isobutyraldehyde (8.0 μL, 0.000088 mol) and sodium triacetoxyborohydride (3.0E1 mg, 0.00014 mol). The resulting solution was stirred at RT for 16 h. The volatiles were removed in vacuo and the resulting residue was dissolved in acetonitrile/H2O and purified by prep.-LC/MS chromatography to afford the desired product. LC-MS: 307.1 (M+1H)+.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resulting residue was dissolved in acetonitrile/H2O
  3. custompurified by prep.-LC/MS chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8c5223cd1979476598927ad65121b715
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998959B2

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