4-Chlorobenzaldehyde → HCID 43087261, compound

HRID 408587Notes

Reaction equation

HRID 408587 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl.[CH3:16][O:17][C:18](=[O:22])[CH2:19][CH2:20][NH2:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:16][O:17][C:18](=[O:22])[CH2:19][CH2:20][NH:21][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 516892Sodium BicarbonateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43087261HCID 43087261, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-chlorobenzaldehyde (1 eq.) in MeOH were added NaHCO3 (1.3 eq.) and (β-alanine methyl ester hydrochloride (1.2 eq.). The reaction was stirred for 15 h at 20° C. under nitrogen, then cooled to 0° C. Sodium triacetoxyborohydride (1.5 eq.) was added portionwise. The reaction was then warmed to 20° C. and stirred for 8 h. The crude was concentrated under reduced pressure then partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/DCM/MeOH: 50/50/0, then 0/100/0, then 0/99/1) to afford 3-(4-chloro-benzylamino)-propionic acid methyl ester.

Workup

  1. temperaturecooled to 0° C
  2. temperatureThe reaction was then warmed to 20° C.
  3. stirringstirred for 8 h
  4. concentrationThe crude was concentrated under reduced pressure
  5. customthen partitioned between EtOAc
  6. extractionThe aqueous layer was extracted twice with EtOAc
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude was purified by chromatography on silica gel (
  11. washelution with heptane/DCM/MeOH

Sources & evidence

ORD record
ord-21a048062acb4fe9a37b779387ddc711
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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