Chloroiodomethane → (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride

HRID 559329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 559329
[CH2:1]([Zn]CC)C.[Cl:6]CI.C(OC([N:16]1[CH2:21][CH2:20][C:19](=[CH2:22])[CH:18]([OH:23])[CH2:17]1)=O)(C)(C)C>ClCCCl>[ClH:6].[CH2:22]1[C:19]2([CH2:20][CH2:21][NH:16][CH2:17][C@H:18]2[OH:23])[CH2:1]1

Komponenten

5

Edukt 3

HCID 11644ChloroiodomethaneHCID 10584700tert-Butyl 3-hydroxy-4-methylidenepiperidine-1-carboxylateHCID 178418750HCID 178418750, Verbindung

Produkt 1

HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochlorideAusbeute 36.664,699 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of diethylzinc (1.1 M solution in toluene, 37.5 ml, 0.04 mmol) in 1,2-dichloroethane (80 ml) at 0° C. was added chloroiodomethane (5.99 ml, 0.08 mmol) under Ar. This mixture was stirred for 15 minutes before a solution of 3-hydroxy-4-methylene-piperidine-1-carboxylic acid tert-butyl ester (J. Org. Chem. 2001, 66, 2487) (4.19 g, 19.6 mmol) in 1,2-dichloroethane (10 ml) was added, after which time the reaction was stirred for 0.5 h at 0° C. and then allowed to reach room temperature, stirring for a further 1 h. The reaction was then quenched by addition of saturated aq. ammonium chloride solution, separated, and the organic dried (Na2SO4) and concentrated. Purification by flash column chromatography (ethyl acetate/heptane 2:8-1:1) afforded the title product (2.4 g, 54%) as a crystalline solid MS: 228.2 (MH+).

Aufarbeitung

  1. additionwas added
  2. customto reach room temperature
  3. stirringstirring for a further 1 h
  4. customThe reaction was then quenched by addition of saturated aq. ammonium chloride solution
  5. customseparated
  6. dry with materialthe organic dried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (ethyl acetate/heptane 2:8-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2e7967a7a7c94bc5bac14bfffe51af8e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063042B2

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