Benzyl Bromide → (1S,3R)-benzyl 3-acetyl-2,2-dimethylcyclobutanecarboxylate

HRID 2179726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179726
[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].C([O-])([O-])=O.[Cs+].[Cs+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CN(C=O)C.CCOC(C)=O>[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][CH2:25][C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 10630987(1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

Produkt 1

HCID 58111012(1S,3R)-benzyl 3-acetyl-2,2-dimethylcyclobutanecarboxylateAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A stirred solution of (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid (6.0 g, 35.29 mmol) in DMF (20 ml) at 0° C., Cs2CO3 (13.8 g, 42.34 mmol) followed by BnBr (5.06 ml, 42.34 mmol) were added slowly portion wise. The reaction was stirred at room temperature for about 2 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc (100 ml) and washed with water (50 ml), brine (50 ml) and dried with Na2SO4. The solvent was evaporated and purified by silica gel column (60-120, elution 4% EtOAc in hexane) to afford title compound as a pale yellow syrup. Wt: 5.6 g; Yield: 61.5%; 1H NMR (300 MHZ, CDCl3): δ 7.42-7.31 (m, 5H), 5.13 (s, 2H), 2.93-2.81 (m, 2H), 2.68 (q, 1H, J=10.5 Hz,), 2.05 (s, 3H), 1.97-1.88 (m, 1H), 1.43 (s, 3H), 0.87 (s, 3H); Mass: [M+1]+ 261 (20%), [M+Na]+ 283 (87%); IR (KBr, cm−1): 2889, 1732, 1708, 1498, 1456, 1329, 1279, 1183, 1027, 954, 752, 698.

Aufarbeitung

  1. customat 0° C.
  2. additionwere added slowly portion wise
  3. customAfter completion of the reaction (monitored by TLC)
  4. washwashed with water (50 ml), brine (50 ml)
  5. dry with materialdried with Na2SO4
  6. customThe solvent was evaporated
  7. custompurified by silica gel column (60-120, elution 4% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1abef5ae2eba443da0c6ff77ab884581
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067966B2

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