Sodium borohydride → HCID 11340988, 화합물

HRID 1064756노트

반응식

HRID 1064756 반응식
[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

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 9884652HCID 9884652, 화합물

생성물 1

HCID 11340988HCID 11340988, 화합물수율 11%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-98127d322f0640f08fae572577f2ef1c
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969730B2

반응 노트

불러오는 중…