Sodium borohydride → HCID 16641709, compound

HRID 536957Notes

Reaction equation

HRID 536957 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>C1COCC1.CCOC(C)=O.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:16][NH2:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 58994987HCID 58994987, compound

Product 1

HCID 16641709HCID 16641709, compound

Reagents, catalysts & solvents 3

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-nitro-phenyl)-tetrahydro-pyran-4-carbonitrile (as prepared in the previous step) in THF is treated with ZrCl4 and NaBH4 (Synthesis, (12), 995-6 (1988)) at RT. The mixture is diluted with EtOAc and washed with water. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue is purified by silica gel chromatography with the appropriate solvent to afford the title compound.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel chromatography with the appropriate solvent

Sources & evidence

ORD record
ord-00f16ec5d9bc454288c7b33ea9317730
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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