Lithium borohydride → 1-(Hydroxymethyl)cyclopentanecarbonitrile
Reaction equation
[C:1]([C:3]1([C:8](OC)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[BH4-].[Li+]>C1COCC1>[OH:9][CH2:8][C:3]1([C:1]#[N:2])[CH2:7][CH2:6][CH2:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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): δ3.62 (s, 2H), 2.39-1.60 (m, 8H).
Workup
- temperatureThe resulting solution was heated
- temperatureto reflux for 3 hours
- customThe mixture was quenched by the addition of water
- extractionwas extracted with ethyl acetate
- dry with materialThe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-0502f59bff154b7da0372a7a30dd4ada
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541425B2
Reaction notes
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