Benzaldehyde, 4-(phenylmethoxy)- → HCID 10827000, compound

HRID 651890Notes

Reaction equation

HRID 651890 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[CH2:8]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 122755Glycine methyl ester hydrochlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10827000HCID 10827000, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of glycine methyl ester hydrochloride (1.26 g, 10 mmol) and 4-benzyloxybenzaldehyde (2.12 g, 10 mmol) in DCM (50 mL), under nitrogen at 0° C., was added Na(OAc)3BH (3.81 g, 15 mmol). The suspension was allowed to warm to room temperature and stirred for 4 hours. The suspension was poured into saturated aqueous NaHCO3, and the layers were separated. The aqueous layer was extracted with DCM (4×25 mL). The combined organic extracts were dried over MgSO4 and concentrated. Flash chromatography (EA) gave 1.15 g (40.4%) of the title compound as a white solid; mp 57-58° C.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with DCM (4×25 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-53f5a90170754eac929082f7b677e6a8
Source dataset
uspto-grants-2001_08
Patent number
US06281194B1

Reaction notes

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