Water → 2-(1-Hydroxy-2-morpholin-4-yl-ethyl)-6,7-dimethyl-benzofuran-5-ol

HRID 480982ノート

反応式

HRID 480982 の反応式
[CH3:1][C:2]1[C:19]([O:20]C(=O)C)=[CH:18][C:5]2[CH:6]=[C:7]([C:9](=[O:17])[CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[O:8][C:4]=2[C:3]=1[CH3:24].[BH4-].[Na+].O>CO>[OH:17][CH:9]([C:7]1[O:8][C:4]2[C:3]([CH3:24])=[C:2]([CH3:1])[C:19]([OH:20])=[CH:18][C:5]=2[CH:6]=1)[CH2:10][N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10236780Acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester

生成物 1

HCID 101930312-(1-Hydroxy-2-morpholin-4-yl-ethyl)-6,7-dimethyl-benzofuran-5-ol収率 68.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of acetic acid 6,7-dimethyl-2-(2-morpholin4-yl-acetyl)-benzofuran-5-yl ester (35 mg), prepared as in Example 17, in MeOH (10 mL) was stirred while NaBH4 (40 mg) was added, and the mixture was stirred at room temperature for an additional 4 h. The mixture was poured into water, and extracted with ethylacetate. The organic layer was dried over MgSO4 and evaporated. The residue was purified by silica gel column eluting with 5% MeOH in DCM to give 21 mg of 2-(1-hydroxy-2-morpholin-4-yl-ethyl)-6,7-dimethyl-benzofuran-5-ol as an oil. Conversion into HCl salt gave a yellow solid. 1H NMR (CD3OD, 300 MHz) δ: 6.77 (s, 1H), 6.67 (s, 1H), 5.29 (dd, J=10.4, 3.3 Hz, 1H), 4.04 (m, 2H), 3.85 (q, 2H), 3.70-3.50 (m, 4H), 3.30 (m, 2H), 2.40 (s, 3H), 2.20 (s, 3H) ppm. 13C NMR (CD3OD, 75 MHz) (as HCl salt) δ: 154.72, 151.88, 149.40, 125.02, 121.67, 120.21, 104.51, 102.50, 63.77, 63.69, 61.70, 60.19, 53.82, 51.28, 11.24, 11.10 ppm. M/S 292 (M+H+).

後処理

  1. additionwas added
  2. extractionextracted with ethylacetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe residue was purified by silica gel column
  6. washeluting with 5% MeOH in DCM

出典と根拠

ORDレコード
ord-cdb1a0faf22e4109aabc9aefad832728
出典データセット
uspto-grants-2003_11
特許番号
US06653346B1

反応ノート

読み込み中…