Lithium borohydride → 6-Hydroxyspiro[2.5]octane-5-carbonitrile

HRID 1852474Notes

Reaction equation

HRID 1852474 reaction equation
[O:1]=[C:2]1[CH2:9][CH2:8][C:5]2([CH2:7][CH2:6]2)[CH2:4][CH:3]1[C:10]#[N:11].[BH4-].[Li+]>C1COCC1.O>[OH:1][CH:2]1[CH2:9][CH2:8][C:5]2([CH2:6][CH2:7]2)[CH2:4][CH:3]1[C:10]#[N:11]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 867310106-Oxospiro[2.5]octane-5-carbonitrile

Product 1

HCID 867310116-Hydroxyspiro[2.5]octane-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-oxospiro[2.5]octane-5-carbonitrile (130 mg, 0.87 mmol) in THF (4.3 mL) was stirred at ambient temperature and lithium borohydride (76 mg, 3.5 mmol) was added. The resulting mixture was stirred at ambient temperature for 16 hours. The mixture was diluted with water and extracted with EtOAc (2×). The combined organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford the title compound. The material was used without further purification.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-713ed157942f44dbadb358a83569b8a8
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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