tert-Butanol → tert-butyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylate

HRID 2179730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179730
[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([OH:10])=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2].[CH3:13][C:14](O)([CH3:16])[CH3:15].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1.CN(C1C=CN=CC=1)C>[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][C:14]([CH3:16])([CH3:15])[CH3:13])=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 10630987(1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

Produkt 1

HCID 21576610tert-butyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a stirred ice cooled solution of (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid (3.0 g, 17.65 mmol) in THF (5 ml), t-BuOH (5.1 ml, 52.94 mmol) and DMAP (0.036 g, 0.176 mmol) in THF (3 ml) were added followed by DCC (4.4 g, 21.2 mmol) in dry THF (2 ml) was added slowly. Then the reaction was stirred at room temperature for about 36 hours. After completion of the reaction (monitored by TLC), the reaction mixture was filtered through a celite bed and washed with DCM. The filtrate was washed with 5% HCl, water, aqueous NaHCO3 and dried over Na2SO4. The solvent was evaporated and purified by silica gel column (60-120, elution 10% EtOAc in hexane) to afford title compound as a pale yellow syrup. Wt: 2.4 g; Yield: 60%; 1H NMR (300 MHZ, CDCl3): δ 2.84 (m, 1H), 2.70-2.51 (m, 2H), 2.06 (s, 3H), 1.89-1.80 (m, 1H), 1.41 (s, 12H), 0.93 (s, 3H); Mass: [M+Na]+ 249 (100%).

Aufarbeitung

  1. additionwas added slowly
  2. customAfter completion of the reaction (monitored by TLC)
  3. filtrationthe reaction mixture was filtered through a celite bed
  4. washwashed with DCM
  5. washThe filtrate was washed with 5% HCl, water, aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated
  8. custompurified by silica gel column (60-120, elution 10% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-495752057c604441a786dd4dfa7c7d40
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067966B2

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