Water → 3-amino-7-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-on

HRID 1033385ノート

反応式

HRID 1033385 の反応式
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:16])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:16]

参加物

5

反応物 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 538629013-Azido-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

生成物 1

HCID 544585903-amino-7-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-on収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-Azido-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (3.36 g, 15.3 mmol) (Step C) dissolved in dry tetrahydrofuran was treated with 4.00 g (15.3 mmol; leq) of triphenylphosphine and the resulting solution stirred at room temperature under nitrogen for 2 hours. Water (0.48 mL, 2eq) was added and the mixtured stirred at room temperature for 16 hours. Solvents were removed under vacuum and the residue purified by preparative HPLC on silica, eluting with methylene chloride/methanol (9:1) to afford 2.39 g (12.3 mmol, 81%) of product. 1H NMR (200MHz, CD3OD): 1.87 (m,1H), 2.41 (m,1H), 2.6-2.9 (m,2H), 3.30 (dd;8,12 Hz;1H), 7.0 (m,3H). FAB-MS: calculated for C10H11FN2O 194; found 195 (M+H,100%).

後処理

  1. stirringthe mixtured stirred at room temperature for 16 hours
  2. customSolvents were removed under vacuum
  3. customthe residue purified by preparative HPLC on silica
  4. washeluting with methylene chloride/methanol (9:1)

出典と根拠

ORDレコード
ord-4fd1a3a423fe4118a6498ff14dfc08c2
出典データセット
uspto-grants-1994_05
特許番号
US05310737

反応ノート

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