cyclobutane-1,2-diol synthesis

Yield: 26.2%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in tetrahydrofuran at 20; for 12 h;

Steps:

228.1 Step 1:
cis-Cyclobutane-1,2-diol

To a solution of 1,2-(trimethylsilyloxy)cyclobutene (3.0 g, 13.02 mmol) in tetrahydrofuran (100 mL) was added Pd/C (10%, 800.0 mg, 6.35 mmol.
The mixture was stirred at under hydrogen at room temperature for 12 hours.
After filtration, the filtrate was concentrated under vacuum.
The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/petroleum ether (2/1) to afford cis-cyclobutane-1,2-diol (300 mg, 3.40 mmol, 26.2% yield) as a colorless oil. ¹H NMR (300 MHz, CDCl₃) δ 4.59 (s, 2H), 4.19 (q, J=3.7 Hz, 2H), 2.17-1.69 (m, 4H).

References:

Genentech, Inc.;LIANG, Jun;MENDONCA, Rohan V.;SIU, Michael;TELLIS, John;WANG, Weiru;WEI, BinQing;CHAN, Bryan;CHOO, Edna F.;DROBNICK, Joy;GAZZARD, Lewis J.;HEFFRON, Timothy US2020/108075, 2020, A1 Location in patent:Paragraph 1528; 1529