Phenylacetaldehyde → HCID 86676363, compound

HRID 1409675Notes

Reaction equation

HRID 1409675 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@H:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:5][CH:4]=1.[C:19]1([CH2:25][CH:26]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@H:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:12][N:11]([CH2:26][CH2:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 998PhenylacetaldehydeHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 86676361HCID 86676361, compound

Product 1

HCID 86676363HCID 86676363, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The product from step A (770 mg, 2.81 mmol) in 1,2-dichloroethane (10 mL) was treated at rt with phenylacetaldehyde (0.987 mL, 8.44 mmol), sodium acetate (231 mg, 2.81 mmol) and sodium triacetoxyborohydride (1.79 g, 8.44 mmol). The mixture was stirred at rt for approximately 18 h, then poured into 1 M sodium hydroxide (10 mL) and extracted with ethyl acetate. The combined organic portions were dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The resulting residue was purified by column chromatography on SiO2 (10% MeOH/methylene chloride) to afford the title compound. HPLC/MS: 342.3 (M+1); Rt=1.00 min (2 minute method).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic portions were dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by column chromatography on SiO2 (10% MeOH/methylene chloride)

Sources & evidence

ORD record
ord-b4abe1996efa414cbfce248fd8425705
Source dataset
uspto-grants-2014_12
Patent number
US08921394B2

Reaction notes

Loading…