Beta-Aminoisobutyric Acid → tert-butyl (6S)-6-formyl-5-azaspiro[2.4]heptane-5-carboxylate

HRID 536590

Reaktionsgleichung

Reaktionsgleichung von HRID 536590
[OH:1][CH2:2][C@@H:3]1[CH2:9][C:6]2([CH2:8][CH2:7]2)[CH2:5][N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].CC1(C)N([O])C(C)(C)CCC1.CC(C(O)=O)CN>C(Cl)Cl>[CH:2]([C@@H:3]1[CH2:9][C:6]2([CH2:7][CH2:8]2)[CH2:5][N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:1]

Komponenten

5

Edukt 3

HCID 64956Beta-Aminoisobutyric AcidHCID 2724126TempoHCID 66848415(S)-Tert-butyl 6-(hydroxymethyl)-5-azaspiro[2.4]heptane-5-carboxylate2×

Produkt 1

HCID 71743236tert-butyl (6S)-6-formyl-5-azaspiro[2.4]heptane-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To (S)-tert-butyl 6-(hydroxymethyl)-5-azaspiro[2.4]heptane-5-carboxylate (Intermediate 59, 2.2 g, 9.7 mmol) dissolved in 10 ml of DCM, TEMPO (306 mg, 1.9 mmol) and BAIB (3.43 mg, 10.6 mmol) were added. After 2 hours at 25° C., the reaction is diluted with DCM (150 ml), washed with an aqueous solution of Na2S2O3 then with water, dried (Na2SO4) and evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5). (S)-tert-butyl 6-formyl-5-azaspiro[2.4]heptane-5-carboxylate was obtained as light yellow solid (1.8 g).

Aufarbeitung

  1. washwashed with an aqueous solution of Na2S2O3
  2. dry with materialwith water, dried (Na2SO4)
  3. customevaporated
  4. customto obtain a crude that
  5. customwas purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-b2ae26e6f70c4220905d296676c2dadc
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859608B2

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