Cyclopentanemethanol, 3-hydroxy-, (1R,3S)-rel- synthesis

6synthesis methods

Product Name:Cyclopentanemethanol, 3-hydroxy-, (1R,3S)-rel-
CAS Number:111292-52-5
Molecular formula:C6H12O2
Molecular Weight:116.16

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Cyclopentanemethanol, 3-hydroxy-, (1R,3S)-rel-

111292-52-5
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Yield:111292-52-5 75%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0; for 1 h;Inert atmosphere;

Steps:

Step B: 3-(hydroxymethyl)cyclopentanol

To a solution of LiAlH4 (721 mg, 18.99 mmol, 3 eq) in THF (20 mL) was added dropwise a solution of methyl 3-oxocyclopentanecarboxylate (900 mg, 6.33 mmol, 1 eq) in THF (5 mL) at 0 °C under N₂. The mixture was stirred at 0 °C for 1 h. The mixture was warmed to 20 °C and stirred for 12 h. The reaction mixture was diluted with THF (20 mL), and then the mixture was quenched with sodium sulfate decahydrate (1 g). The mixture was filtered and the filtrate was concentrated in vacuum. The residue was purified by FC (PE : EtOAc 3:1 to 0:1) to give the title compound (550 mg, 75% yield) as a yellow oil. ¹H NMR (DMSO-d6): d 4.43-4.38 (m, 2 H), 4.05-4.02 (m, 1 H), 3.33-3.31 (m, 1 H), 3.25- 3.22 (m, 1 H), 1.96-1.81 (m, 2 H), 1.61-1.55 (m, 2 H), 1.47-1.36 (m, 2 H) and 1.16-1.09 (m, 1 H).

References:

WO2021/32591,2021,A1 Location in patent:Page/Page column 147-148

67-47-0 Synthesis