Triphenylphosphine → (2S)-3-Phenylpropane-1,2-diamine

HRID 650678

반응식

HRID 650678 반응식
[N:1]([CH2:4][C@@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C@@H:5]([NH2:13])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 11769078(S)-1-azido-3-phenylpropan-2-amine

생성물 1

HCID 12699301(2S)-3-Phenylpropane-1,2-diamine수율 65.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A sample of the compound from step 4a (790 mg, 4.48 mmole) was dissolved in 30 mL of THF and 6 mL of water, triphenylphosphine (5.0 g, 19.1 mmole) was added, and the reaction mixture was stfired for 24 hours at reflux. The solvent was removed, and the residue was dissolved in 2 N HCl. NaCl was added, and the solution was extracted with ethyl ether. The aqueous layer was adjusted to pH 12 with K2CO3, saturated with NaCl, then extracted with GICl3 and CHCl3 containing 15% isopropanol. The solvent was removed under vacuum to afford 439 mg of the title compound. MS m/z (M+H)+: 151, MS m/z (M+NH4)+: 168.

후처리

  1. temperatureat reflux
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in 2 N HCl
  4. additionNaCl was added
  5. extractionthe solution was extracted with ethyl ether
  6. extractionextracted with GICl3 and CHCl3 containing 15% isopropanol
  7. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-afb21f95af18418e86f0c6e3317b7bc5
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274715B1

연결된 노트

불러오는 중…