1,4-Dioxane → (1R,3S)-3-[(tert-Butoxy)carbonyl]-2,2-dimethylcyclobutane-1-carboxylic acid
Reaction equation
[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]1([CH3:16])[CH3:15])(=[O:3])C.[O:17]1CCOCC1>>[C:11]([O:10][C:8]([C@H:6]1[CH2:7][C@@H:4]([C:1]([OH:3])=[O:17])[C:5]1([CH3:16])[CH3:15])=[O:9])([CH3:14])([CH3:13])[CH3:12]Participants
Procedure
A stirred solution of (1S,3R)-tert-butyl 3-acetyl-2,2-dimethylcyclobutanecarboxylate (2.4 g, 10.62 mmol) in dioxane (270 ml) aqueous NaOBr solution (about 180 ml) was added slowly at about 0° C. and stirred at the same temperature for about 3 hours then allowed to stirred at room temperature for about 4 hours (the yellow colored solution turned to white color). After completion of the reaction (monitored by TLC), the reaction mixture was washed with methyl t-butyl ether (3×150 ml), the aqueous layer was adjusted pH (2-3) with 1N HCl and the aqueous layer was extracted with EtOAc and dried over Na2SO4 and the solvent was evaporated to afford title compound as an off white liquid. Wt: 1.9 g; Yield: 78%; 1H NMR (300 MHZ, CDCl3): δ 2.82-2.67 (m, 2H), 2.57-2.50 (m, 1H), 2.04-1.98 (m, 1H), 1.42 (s, 9H), 1.34 (s, 3H), 1.05 (s, 3H); IR (KBr, cm−1): 3205, 1731, 1694, 1460, 1371, 1236, 1157, 1108, 846, 721; Mass: [M+Na]+ 251 (40%).
Workup
- stirringto stirred at room temperature for about 4 hours (the yellow colored solution
- customAfter completion of the reaction (monitored by TLC)
- washthe reaction mixture was washed with methyl t-butyl ether (3×150 ml)
- extractionthe aqueous layer was extracted with EtOAc
- dry with materialdried over Na2SO4
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-e15d15d574074ea9ac266c67a5079182
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067966B2
Reaction notes
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