Sodium cyanoborohydride → HCID 19018529, compound

HRID 1109988Notes

Reaction equation

HRID 1109988 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[O:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9]([CH2:11][CH3:12])=[N:10][C:4]=2[CH:3]=1.[BH3-]C#N.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[O:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[CH:9]([CH2:11][CH3:12])[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 19018521HCID 19018521, compound

Product 1

HCID 19018529HCID 19018529, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of the title compound of Example 15 in THF was added NaCNBH3. The reaction was stirred for 24 hours at room temperature. The solvent was removed under reduced pressure, and the residue was taken up in CHCl3 with HCl (1M, 25 mL). The resulting mixtures were stirred for 1 hour at room temperature. The CHCl3 was separated, extracted with NaHCO3 (saturated) and brine. The solvent was removed to yield a yellow oil (2.06 g). The material was purified by column chromatography on silicagel 15/85 EtOAc/hexane to yield 1.06 g of the title compound. This material was employed in Example 17 without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. stirringThe resulting mixtures were stirred for 1 hour at room temperature
  3. customThe CHCl3 was separated
  4. extractionextracted with NaHCO3 (saturated) and brine
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-36353a1349b4461aaa8f852716718984
Source dataset
uspto-grants-1994_06
Patent number
US05324722

Reaction notes

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