Sodium borohydride → HCID 19088660, compound

HRID 1463836Notes

Reaction equation

HRID 1463836 reaction equation
[CH:1]1([N:7]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[C:11]([CH3:17])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([N:7]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([CH3:17])[CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53901059HCID 53901059, compound

Product 1

HCID 19088660HCID 19088660, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The aldehyde XXXIV of Scheme K (1.70 g, 0.0052 moles) was dissolved in 20 mls of MeOH and cooled to 0° C. under argon. NaBH4 (110 mg) was added and the mixture was allowed to warm to 25° C. Excess solvent was removed under vacuum and the residue was treated with water and ethyl acetate. The organic layer was separated and dried (Na2SO4). Removal of the solvent on the rotary evaporator gave a residue which was chromatographed on silica gel using 30% ethyl acetate/hexane as the eluent to give 1.75 g (96%) of the title compound as an oil. NMR (ppm, CDCl3): 2.28 (3H, s); 4.65 (2H, s); 7.10 (1H, d, J=8 Hz); 7.15 (1 h, s); 7.30 (1 h, d, J=8 Hz).

Workup

  1. temperatureto warm to 25° C
  2. customExcess solvent was removed under vacuum
  3. additionthe residue was treated with water and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent
  7. customon the rotary evaporator
  8. customgave a residue which
  9. customwas chromatographed on silica gel using 30% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-6fc3af6e0bb44dfdb6b64373ea6d79fa
Source dataset
uspto-grants-1994_04
Patent number
US05302601

Reaction notes

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