2-Amino-2-phenylethan-1-ol → (3S,7aS)-7a-cyclopropyl-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one

HRID 406487ノート

反応式

HRID 406487 の反応式
[NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[CH:11]1([C:14](=O)[CH2:15][CH2:16][C:17](O)=[O:18])[CH2:13][CH2:12]1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH:11]1([C@@:14]23[CH2:15][CH2:16][C:17](=[O:18])[N:1]2[C@@H:2]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][O:4]3)[CH2:13][CH2:12]1

参加物

5

反応物 2

HCID 1347972-Amino-2-phenylethan-1-olHCID 162137294-Cyclopropyl-4-oxobutanoic acid

生成物 1

HCID 59764671(3S,7aS)-7a-cyclopropyl-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one収率 75.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of (S)-2-amino-2-phenylethanol (2.28 g, 16.6 mmol) and 4-cyclopropyl-4-oxobutanoic acid (1.97 g, 13.8 mmol) in toluene (35 mL) was heated at reflux for about 6 h. The reaction mixture was cooled to room temperature and diluted with EtOAc, washed with aqueous HCl (1.0 N), saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified on a Biotage silica gel column eluting with heptane/EtOAc (3:2) to afford (3S,7aS)-7a-cyclopropyl-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one (2.54 g, 10.4 mmol) as a bright yellow needle-like solid. RP-HPLC (Table 1, Method a) Rt 1.77 min; m/z: (M+H)+ 244.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for about 6 h
  3. washwashed with aqueous HCl (1.0 N), saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on a Biotage silica gel column
  8. washeluting with heptane/EtOAc (3:2)

出典と根拠

ORDレコード
ord-5b62b187d7964388890c08ebf9a8995b
出典データセット
uspto-grants-2014_06
特許番号
US08754107B2

反応ノート

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