Hydrochloric Acid → (2R)-3-Phenylpropane-1,2-diamine

HRID 351340

Reaction equation

HRID 351340 reaction equation
[NH2:1][C@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]#[N:4].Cl.[H][H].N[C@H](CC1C=CC=CC=1)CO>CO.O.[Pd]>[C:6]1([CH2:5][C@@H:2]([NH2:1])[CH2:3][NH2:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 853475phenylalaninol, (R)-HCID 12113026(2R)-2-Amino-3-phenylpropanenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 12699299(2R)-3-Phenylpropane-1,2-diamineYield 6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 9.0 g (49 mmol) of (R)-2-amino-3-phenylpropionitrile.HCl-salt (97.5% e.e.) in 280 mL of methanol-water 1:1 was added 2.2 equiv. of conc. HCl solution and 2.0 g of 5% Pd/C. The solution was hydrogenated for 19 h at 35° C. and 0.9 MPa of hydrogen pressure. Then additional 2 g of Pd/C was added and hydrogenation was continued for 24 h at 3.0 MPa. According to chiral HPLC 91% of (R)-2-amino-3-phenyl-1-propanol was formed together with 6% of (R)-3-phenyl-1,2-diaminopropane The reaction mixture was filtered and partially evaporated. The solution was basified to pH 10 using diluted NaOH solution and extracted with CH2CL2. The organic solution was dried over Na2SO4 and evaporated.

Workup

  1. waithydrogenation was continued for 24 h at 3.0 MPa

Sources & evidence

ORD record
ord-7098506dc436431584fa78b5060cb395
Source dataset
uspto-grants-2007_02
Patent number
US07183443B2

Linked notes

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