Benzaldehyde → HCID 131729001, compound

HRID 1010883Notes

Reaction equation

HRID 1010883 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:20])[CH2:17][NH:18][CH3:19])=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:21])[NH:7][C@H:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:20])[CH2:17][N:18]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:19])=[CH:14][CH:15]=1)[CH3:9])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 131729000HCID 131729000, compound

Product 1

HCID 131729001HCID 131729001, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The compound [2-3] was dissolved in 3 mL of chloroform, and 76 μL of benzaldehyde and 158 mg of sodium triacetoxyborohydride were added thereto. After an overnight stirring at room temperature, to the mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of chloroform and methanol (mixing ratio: 9/1). The resulting organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and then the resulting residue was purified by preparative thin-layer chromatography, to obtain 64 mg of tert-butyl{(1S)-1-[4-(N-benzyl-N-methylglycyl)phenyl]ethyl}carbamate [24] (hereinafter, referred to as the compound [2-4]) as a colorless oily product.

Workup

  1. extractionthe mixture was extracted with a mixed solvent of chloroform and methanol (mixing ratio: 9/1)
  2. washThe resulting organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insolubles were filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-5d6f2df795db422e92cb8850af0cbb87
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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