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

HRID 650678

反応式

HRID 650678 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-afb21f95af18418e86f0c6e3317b7bc5
出典データセット
uspto-grants-2001_08
特許番号
US06274715B1

関連ノート

読み込み中…