Sodium cyanoborohydride → HCID 19018527, compound

HRID 1109989Notes

Reaction equation

HRID 1109989 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[O:6][C:7]3[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=3[C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:4]=2[CH:3]=1.[BH3-]C#N.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[O:6][C:7]3[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=3[CH:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 19018524HCID 19018524, compound

Product 1

HCID 19018527HCID 19018527, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of the title compound of Example 19 (2.6 g) in THF (100 mL) was added NaCNBH3 (1.0 g). The reaction was stirred for 24 hours. The solvent was removed under reduced pressure, and the residue was taken up in CHCl3 with HCl (1M, 25 mL). The resulting mixture was stirred for 1 hour at room temperature. The CHCl3 was separated, extracted with NaHCO3 (saturated) and brine. The solvent was then removed to yield a yellow oil (2.5 g). This material was purified by column chromatography to yield 1.7 g of the title compound. This material was employed in Example 21 without further purification.

Workup

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

Sources & evidence

ORD record
ord-77a4a490c0404d07853fd0d7ffa5258f
Source dataset
uspto-grants-1994_06
Patent number
US05324722

Reaction notes

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