Lithium borohydride → 1-(Hydroxymethyl)cyclopentanecarbonitrile

A mixture of methyl 1-cyanocyclopentanecarboxylate (prepared in Example 740, Step 1) (500 mg, 3.0 mmol) in THF (7 mL) was treated with lithium tetrahydroborate (100 mg, 6.0 mmol). The resulting solution was heated to reflux for 3 hours, then stirred at ambient temperature for 16 hours. The mixture was quenched by the addition of water, and was extracted with ethyl acetate. The combined organic extracts were dried over Na2SO4, then filtered and the solvent was removed in vacuo to afford the product (387 mg, 95%). 1H NMR (300 MHz, CDCl3): δ 3.62 (s, 2H), 2.39-1.60 (m, 8H).

1. temperatureThe resulting solution was heated
2. temperatureto reflux for 3 hours
3. customThe mixture was quenched by the addition of water
4. extractionwas extracted with ethyl acetate
5. dry with materialThe combined organic extracts were dried over Na2SO4
6. filtrationfiltered
7. customthe solvent was removed in vacuo

ORD record

ord-71f6f94bae8345daa44336180f0f5be9

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933086B2