Water → HCID 71239740, compound

HRID 587125Notes

Reaction equation

HRID 587125 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][C:14]([C:22]#[N:23])([C:17](OCC)=[O:18])[CH2:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>C1COCC1.O.C1COCC1>[CH2:3]([O:10][CH:11]1[CH2:16][CH2:15][C:14]([CH2:17][OH:18])([C:22]#[N:23])[CH2:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 71239678HCID 71239678, compound

Product 1

HCID 71239740HCID 71239740, compoundYield 116.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of sodium borohydride (186 mg, 4.92 mmol, 2.5 equiv) in THF/H2O (5/0.5 mL) was added a solution of ethyl 4-(benzyloxy)-1-cyanocyclohexanecarboxylate (565 mg, 1.97 mmol, 1.0 equiv) in THF (dry, 3 mL) dropwise. The reaction mixture was stirred at room temperature for 18 hrs. It was concentrated to give the white solid. H2O (20 mL) was added. The aqueous phase was extracted with EtOAc (4×30 mL). The combined organic solution was washed with brine (30 mL), dried over anhydrous Na2SO4 and then concentrated to give 565 mg of crude 4-(benzyloxy)-1-(hydroxymethyl)cyclohexanecarbonitrile as a colorless sticky oil which was not purified and submitted for the next reaction.

Workup

  1. concentrationIt was concentrated
  2. customto give the white solid
  3. extractionThe aqueous phase was extracted with EtOAc (4×30 mL)
  4. washThe combined organic solution was washed with brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b79e2a669da64a5c9ca0ec84cab1682b
Source dataset
uspto-grants-2016_01
Patent number
US09226923B2

Reaction notes

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