tert-Butanol → tert-butyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylate
Reaction equation
[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].C1COCC1.C1CCC(N=C=NC2CCCCC2)CC1.[C:33](O)([CH3:36])([CH3:35])[CH3:34]>CCOC(C)=O>[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([O:10][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred ice cooled solution of (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid (16.0 g, 94.117 mmol) in THF (160 ml) DMAP (1.148 g, 9.409 mmol) and DCC (23.265 g, 112.93 mmol) were added, followed by t-butyl alcohol (27.63 ml, 282.34 mmol) was added drop wise. The reaction mixture was stirred at room temperature for 36 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc and filtered through a celite bed and washed with EtOAc. The filtrate was as such concentrated and purified by silica gel column (100-200 mesh, elution 10% EtOAc in hexane) to afford the title compound as a solid. Wt: 15.0 g: Yield: 70%; 1H NMR (300 MHz, CDCl3): δ 2.86-2.74 (m, 1H), 2.70-2.50 (m, 2H), 2.04 (s, 3H), 1.89-1.78 (m, 1H), 1.42, 1.40 (2s, 12H), 0.91 (s, 3H); Mass: [M+Na]+ 249 (100%).
Workup
- additionwas added drop wise
- customAfter completion of the reaction (monitored by TLC)
- filtrationfiltered through a celite bed
- washwashed with EtOAc
- concentrationas such concentrated
- custompurified by silica gel column (100-200 mesh, elution 10% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-d13f62ef13df4444948a3f32e6e360ae
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067966B2
Reaction notes
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