Hydrochloric Acid → (2R)-4-phenylbutan-2-amine hydrochloride

HRID 484772Notes

Reaction equation

HRID 484772 reaction equation
C(OC(N[C@@H](C(O)=O)C)=O)(C)(C)C.[N+](=C)=[N-].COC(=O)[C@@H](C)NC(OC(C)(C)C)=O.[H-].C([Al+]CC(C)C)C(C)C.C(OC(N[C@@H](C=O)C)=O)(C)(C)C.C(=C1C=CC=CC1[PH+](C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.[ClH:79].C(OC([NH:87][C@H:88]([CH3:97])[CH2:89][CH2:90][C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1)=O)(C)(C)C>[Pd].O1CCOCC1.CO>[ClH:79].[CH3:97][C@@H:88]([NH2:87])[CH2:89][CH2:90][C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1

Participants

12

Reactant 8

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 637606BOC-D-alanineHCID 637612Boc-D-alanine methyl esterHCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamateHCID 21225700DiisobutylaluminumhydrideHCID 25171954(R)-N-(tert-butyloxycarbonyl)-1-methyl-3-phenylpropanamineHCID 86740214Benzylidenetriphenylphosphonium

Product 1

HCID 15620711(2R)-4-phenylbutan-2-amine hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

(R)-1-Methyl-3-phenylpropanamine hydrochloride was prepared by first esterifying N-(tert-butyloxycarbonyl)-D-alanine with diazomethane, then reducing the resulting N-(tert-butyloxycarbonyl)-D-alanine methyl ester with diisobutylaluminum hydride, then condensing the resulting N-(tert-butyloxycarbonyl)-D-alaninal with benzylidenetriphenylphosphonium ylide, then hydrogenating over palladium catalyst the resulting [R-(E)]-N-(tert-butyloxycarbonyl)-1-methyl-3-phenyl-2-propenamine having m.r. 86°-88° C. and [α]D25 +54.0° (c=1, methanol), and finally deprotecting with hydrogen chloride in dioxane the resulting (R)-N-(tert-butyloxycarbonyl)-1-methyl-3-phenylpropanamine having m.r. 74°-76° C. and [α]D25 +7.2° (c=1, methanol). ##STR16##

Sources & evidence

ORD record
ord-cabc37db756547118196e3a3e22c7ec9
Source dataset
uspto-grants-1985_08
Patent number
US04533657

Reaction notes

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