Sodium borohydride → HCID 11340988、化合物

HRID 1064756ノート

反応式

HRID 1064756 の反応式
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([C:24](=[O:26])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1.[BH4-].[Na+]>C(O)C.O1CCCC1>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([CH:24]([OH:26])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 9884652HCID 9884652、化合物

生成物 1

HCID 11340988HCID 11340988、化合物収率 11%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The product from Example 136C (46 mg, 0.12 mmol) in ethanol (2 mL) and tetrahydrofuran (0.5 mL) was treated with sodium borohydride. The mixture was concentrated and passed through a short column of silica with a gradient of 2 to 10% MeOH/CH2Cl2. The resulting residue rinsed with ether, dissolved into methanol (1 mL), treated with 0.1 M aqueous hydrochloric acid (0.2 mL) heated at 60□ C for three hours, treated with more 0.1 M aqueous hydrochloric acid (0.05 mL), heated at 60□ C for one hour, concentrated, and chromatographed through a short column of silica with a gradient of 2 to 10% 2 M NH3 in MeOH/CH2Cl2 to provide the title compound as a white powder (11% yield). 1HNMR (300 MHz, CD3OD) δ 1.17 (d, 3 H), 1.4-1.54 (m, 1 H), 1.49 (d, 3 H), 1.73-1.86 (m, 2 H), 1.95-2.08 (m, 1 H), 2.24-2.36 (m, 1 H), 2.43-2.60 (m, 2 H), 2.93-3.14 (m, 2 H), 3.19-3.33 (m, 2H), 4.89 (q, 1 H), 6.59 (s, 1 H), 7.32 (ddd, 1 H), 7.39 (dd, 1 H), 7.45-7.47 (m, 2 H), 7.49 (ddd, 1 H), 7.62 (m, 1 H), 7.71 (dd, 1 H).

後処理

  1. concentrationThe mixture was concentrated
  2. washThe resulting residue rinsed with ether
  3. dissolutiondissolved into methanol (1 mL)
  4. additiontreated with 0.1 M aqueous hydrochloric acid (0.2 mL)
  5. temperatureheated at 60□ C for three hours
  6. additiontreated with more 0.1 M aqueous hydrochloric acid (0.05 mL)
  7. temperatureheated at 60□ C for one hour
  8. concentrationconcentrated
  9. customchromatographed through a short column of silica with a gradient of 2 to 10% 2 M NH3 in MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-98127d322f0640f08fae572577f2ef1c
出典データセット
uspto-grants-2005_11
特許番号
US06969730B2

反応ノート

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