Lithium borohydride → 1-(Hydroxymethyl)cyclopentanecarbonitrile

HRID 45047Notes

Reaction equation

HRID 45047 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]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 22736532Methyl 1-cyanocyclopentane-1-carboxylate

Product 1

HCID 566871891-(Hydroxymethyl)cyclopentanecarbonitrileYield 103.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  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

Sources & evidence

ORD record
ord-0502f59bff154b7da0372a7a30dd4ada
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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