Triacetoxyperiodinane → tert-Butyl N-(3-formylcyclohexyl)carbamate

HRID 712036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712036
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:4]1)=[O:1]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 22106830tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate

Produkt 1

HCID 86717490tert-Butyl N-(3-formylcyclohexyl)carbamateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl [3-(hydroxymethyl)cyclohexyl]carbamate (0.51 g, 2.2 mmol) in methylene chloride (10 mL) at 0° C. was added Dess-Martin periodinane (1.1 g, 2.7 mmol). The mixture was stirred at room temperature for 2 h. The reaction was quenched with aq. 1N NaOH solution and extracted with methylene chloride. The combined organic layers were washed with water and then brine, dried over MgSO4, concentrated, and then purified on silica gel column (eluting with 20-50% EtOAc in hexanes) to give the desired product (0.3 g, 59%). LCMS calculated for C12H21NO3Na (M+Na)+: m/z=250.2. Found: 250.1.

Aufarbeitung

  1. customThe reaction was quenched with aq. 1N NaOH solution
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel column (eluting with 20-50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c041ab20dc7d4b129b23dfde65ddf302
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181271B2

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