Diisobutylaluminum hydride → 2-Methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanal

HRID 1501865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1501865
[CH3:1][C:2]([N:9]1[CH2:19][CH2:18][C:12]2([C:16](=[O:17])[NH:15][CH2:14][CH2:13]2)[CH2:11][CH2:10]1)([CH3:8])[C:3](OCC)=[O:4].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:8][C:2]([N:9]1[CH2:19][CH2:18][C:12]2([C:16](=[O:17])[NH:15][CH2:14][CH2:13]2)[CH2:11][CH2:10]1)([CH3:1])[CH:3]=[O:4]

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 86709536Ethyl 2-methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanoate

Produkt 1

HCID 867095372-Methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanoate (3.77 g, 14.1 mmol) in toluene (100 mL) at −78° C. was added DIBAL-H (45.0 mL, 45.0 mmol) dropwise. After 2 h, the reaction was quenched by addition of methanol (10 mL) dropwise, after warmed to rt, 30 mL of saturated sodium sulfate solution was added and the mixture was vigorously stirred at rt for 1 h. After filtration, the filtrate and the filter cake were partitioned between DCM and saturated sodium bicarbonate, the alkaline phase was extracted with DCM three times, the combined organic phase was dried over sodium sulfate, concentrated to give the title compound. LC/MS (M+1+18)+: 243.3; (M+1+32)+: 257.4.

Aufarbeitung

  1. customthe reaction was quenched by addition of methanol (10 mL) dropwise
  2. addition30 mL of saturated sodium sulfate solution was added
  3. filtrationAfter filtration
  4. customthe filtrate and the filter cake were partitioned between DCM and saturated sodium bicarbonate
  5. extractionthe alkaline phase was extracted with DCM three times
  6. dry with materialthe combined organic phase was dried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a91fbd362270402aa32bd5957795bad5
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206198B2

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