HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (2S)-4-phenylbutan-2-amine hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diazomethane | HCID 9550 | — |
| Reactant | Tert-butoxycarbonylalanine | HCID 85082 | — |
| Reactant | tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate | HCID 7015728 | — |
| Reactant | Boc-L-alanine methyl ester | HCID 10856577 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | (S)-N-(tert-butyloxycarbonyl)-1-methyl-3-phenylpropanamine | HCID 54302854 | — |
| Reactant | Benzylidenetriphenylphosphonium | HCID 86740214 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (2S)-4-phenylbutan-2-amine hydrochloride | HCID 15620712 | — |
Reaction Steps
(S)-1-Methyl-3-phenylpropanamine hydrochloride was prepared by first esterifying N-(tert-butyloxycarbonyl)-L-alanine with diazomethane, then reducing the resulting N-(tert-butyloxycarbonyl)-L-alanine methyl ester with diisobutylaluminum hydride, then condensing the resulting N-(tert -butyloxycarbonyl)-L-alaninal with benzylidenetriphenylphosphonium ylide, then hydrogenating over palladium catalyst the resulting [S-(E)]-N-(tert-butyloxycarbonyl)-1-methyl-3-phenyl-2-propenamine having m.r. 86°-88° C. and [α]D25 (c=1, methanol) -50.9°, and finally deprotecting with hydrogen chloride in dioxane the resulting (S)-N-(tert-butyloxycarbonyl)-1-methyl-3-phenylpropanamine having m.r. 78°-80° C. and [α]D25 -7.1° (c=1, methanol). ##STR13##
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04533657 |
| Source dataset | uspto-grants-1985_08 |
| ORD ID | ord-c0f16bff577743dbac59b098d072e5e1 |
| Source note | uspto-grants-1985_08 |