(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate → (1S,3R)-3-acetamido-2,2-dimethylcyclobutane-1-carboxylic acid

HRID 2179728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179728
[C:1]([NH:4][C@@H:5]1[CH2:8][C@H:7]([C:9]([O:11]CC2C=CC=CC=2)=[O:10])[C:6]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([NH:4][C@@H:5]1[CH2:8][C@H:7]([C:9]([OH:11])=[O:10])[C:6]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 86650107(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate

Produkt 1

HCID 11183048(1S,3R)-3-acetamido-2,2-dimethylcyclobutane-1-carboxylic acidAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A stirred solution of (1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate (0.650 g, 2.36 mmol) in EtOAc (10 ml) at room temperature, 10% Pd/C (catalytic amount) were added and the reaction mixture was stirred under H2 gas atmosphere at room temperature for about 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was filtered through celite bed. The obtained filtrate was concentrated under reduced pressure to afford title compound as an off white solid. Wt: 0.240 g; Yield: 54.9%; 1H NMR (300 MHZ, CD3OD): δ 8.09 (d, J=3.0 Hz, 1H), 4.08-3.96 (m, 1H), 2.62-2.58 (m, 1H), 2.20-2.15 (m, 2H), 1.93 (s, 3H), 1.26 (s, 3H), 0.92 (s, 3H); Mass: [M+1]+ 186 (70%), [M+Na]+ 208 (93%). IR (KBr, cm−1): 3349, 2962, 1697, 1624, 1557, 1428, 1377, 1257, 1075, 988, 920, 736; M.R: 194.7° C.-216.2° C.

Aufarbeitung

  1. customAfter completion of the reaction (monitored by TLC)
  2. filtrationthe reaction mixture was filtered through celite bed
  3. concentrationThe obtained filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-36ff39b084814270ae1bb442be98ed00
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067966B2

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