Ammonia → HCID 66852357, compound

HRID 1631196Notes

Reaction equation

HRID 1631196 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].COC(OC)OC.[C:16]1([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29](/[C:32](/[CH3:36])=[CH:33]/[CH:34]=O)=[CH:28][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH4-].[Na+].[ClH:39].N>CO.O1CCCC1.O.C(Cl)(Cl)Cl>[ClH:39].[C:16]1([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:27]=[CH:28][C:29](/[C:32](/[CH3:36])=[CH:33]/[CH2:34][NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[CH:30][CH:31]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

12

Reactant 7

HCID 222AmmoniaHCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86762571HCID 86762571, compound

Product 1

HCID 66852357HCID 66852357, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent3×HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of β-alanine (433 mg) in methanol (30 ml), sodium hydroxide (204 mg) was added. Then, trimethoxymethane (532 μl) was added to the mixture at 0° C. Further, a solution of (2E)-3-[4-(3-phenylpropoxy)phenyl]but-2-enal (1.43 g) in a mixture of methanol (30 ml) and tetrahydrofuran (10 ml) was added. The reaction mixture was stirred at 0° C. for 30 minutes. To the mixture, sodium borohydride (221 mg) was added at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes. After adding 2 N hydrochloric acid (5.5 ml), the reaction mixture was concentrated. To the residue thus obtained, a mixed solvent of chloroform:methanol:aqueous ammonia=80:10:1 was added, followed by filtration. To the precipitate thus obtained, water was added and the mixture was centrifuged to give a precipitate. The obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4). To a suspension of the purified product in dioxane (100 ml) and water (15 ml), a 4 mol/l hydrogen chloride-dioxane solution (0.9 ml) was added at 0° C. The reaction mixture was concentrated and the residue was washed with diethyl ether and dried to give the title compound (1.16 g) having the following physical properties.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  4. concentrationthe reaction mixture was concentrated
  5. customTo the residue thus obtained
  6. filtrationfollowed by filtration
  7. customTo the precipitate thus obtained
  8. customto give a precipitate
  9. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4)
  10. additionTo a suspension of the purified product in dioxane (100 ml)
  11. additionwater (15 ml), a 4 mol/l hydrogen chloride-dioxane solution (0.9 ml) was added at 0° C
  12. concentrationThe reaction mixture was concentrated
  13. washthe residue was washed with diethyl ether
  14. customdried

Sources & evidence

ORD record
ord-0661c8ab41494c82af0017f65e0234fb
Source dataset
uspto-grants-2014_07
Patent number
US08791159B2

Reaction notes

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