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

HRID 351340

반응식

HRID 351340 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 22242641Methanol--water (1/1)용매

실험 절차

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.

후처리

  1. waithydrogenation was continued for 24 h at 3.0 MPa

출처 및 근거

ORD 기록
ord-7098506dc436431584fa78b5060cb395
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183443B2

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