Sodium borohydride → HCID 178511297, compound

HRID 245990Notes

Reaction equation

HRID 245990 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]#[N:7])[CH2:3]1.[BH4-].[Na+]>CO>[O:1]=[C:2]1[CH2:5][CH:4]([C:6]#[N:7])[CH2:3]1.[OH:1][C@@H:2]1[CH2:5][C@H:4]([C:6]#[N:7])[CH2:3]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 130823903-Oxocyclobutane-1-carbonitrile

Product 2

HCID 130823903-Oxocyclobutane-1-carbonitrileHCID 178511297HCID 178511297, compoundYield 163.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Oxocyclobutanecarbonitrile was prepared according to Elend, D.; Fengas, D.; Fray, J. M. Synthetic Communications, 2005, 35, 657. To a solution of 3-oxocyclobutanecarbonitrile (600 mg, 6.31 mmol) in MeOH (25 mL) at 0° C. was slowly added sodium borohydride (263 mg, 6.94 mmol). The reaction mixture was stirred at 0° C. for 1 h then quenched with water and brine and extracted with EtOAc (3×). The combined organics were dried over MgSO4 and concentrated to afford 500 mg (82%) of cis-3-hydroxy-cyclobutanecarbonitrile as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 4.26 (quin, J=7.5 Hz, 1H), 2.70-2.82 (m, 2H), 2.50-2.66 (m, 1H), 2.26-2.41 (m, 2H), 2.09 (br. s., 1H).

Workup

  1. customat 0° C.
  2. customthen quenched with water and brine
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac6f4279b71649f4b040a7d539ac01f2
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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