2,2-Diphenylethylamine → HCID 21710271, compound

HRID 1857925Notes

Reaction equation

HRID 1857925 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Rh]>[CH:10]1([CH:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:8][NH2:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

3

Reactant 1

HCID 775752,2-Diphenylethylamine

Product 1

HCID 21710271HCID 21710271, compound

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

Most Boc-amino acids used in the peptide syntheses are commercially available. 2-methyltyrosine (Mmt) was prepared by catalytic hydrogenation (Pd/C) of 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (7-OH-Tic) in AcOH under H2 pressure at 3 atm. 2',6'-dimethyltyrosine (Dmt) was prepared as described by J. H. Dygos et al. Synthesis, No. 8 (August) pp. 741-743 (1992). Most of the C-terminal amine substituents were also commercially available. 2-(2-bromophenyl)ethylamine, 2-(2-methylphenyl)ethylamine and 2,2-diphenylpropylamine were prepared by reduction of the corresponding nitriles with lithium aluminum hydride, as described by L. M. Amundsen and L. S. Nelson J. Am. Chem. Soc. 73, 242 (1951). 2-(2-biphenyl)ethylamine was synthesized as described by S. Goldschmidt and W. L. C. Veer Recueil 67, 489 (1948). Ethyl-α-phenyl-β-aminopropionate in racemic form was synthesized as described by E. Testa et al. Liebig's Ann. Chem. 614, 167 (1958). Acid hydrolysis of the latter product and subsequent amidation afforded racemic α-phenyl-β-aminopropionamide. 2,2-dicyclohexylethylamine was prepared from 2,2-diphenylethylamine by catalytic hydrogenation (Rh on carbon) at 6° C. under pressure (60 psi).

Sources & evidence

ORD record
ord-a505e5e3c3114cc080f12ceaaa2a379d
Source dataset
uspto-grants-2000_11
Patent number
US06150335

Reaction notes

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