Hydrochloric Acid → (2S)-4-phenylbutan-2-amine hydrochloride
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]=1Participants
12
Reactant 8
HCID 313Hydrochloric Acid
HCID 9550Diazomethane
HCID 85082Tert-butoxycarbonylalanine
HCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate
HCID 10856577Boc-L-alanine methyl ester
HCID 21225700Diisobutylaluminumhydride
HCID 54302854(S)-N-(tert-butyloxycarbonyl)-1-methyl-3-phenylpropanamine
HCID 86740214BenzylidenetriphenylphosphoniumProduct 1
Reagents, catalysts & solvents 3
Procedure
(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##
Sources & evidence
- ORD record
- ord-c0f16bff577743dbac59b098d072e5e1
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04533657
Reaction notes
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