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

HRID 351340

反応式

HRID 351340 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 22242641Methanol--water (1/1)溶媒

実験手順

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.

後処理

  1. waithydrogenation was continued for 24 h at 3.0 MPa

出典と根拠

ORDレコード
ord-7098506dc436431584fa78b5060cb395
出典データセット
uspto-grants-2007_02
特許番号
US07183443B2

関連ノート

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