Sodium Hydroxide → Dihydrocholesterol

HRID 1721305

반응식

HRID 1721305 반응식
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1.CO>[CH3:26][CH:24]([CH2:23][CH2:22][CH2:21][C@H:20]([C@@H:19]1[C@:28]2([CH3:36])[C@H:16]([C@H:15]3[C@H:31]([CH2:30][CH2:29]2)[C@:32]2([CH3:35])[C@H:12]([CH2:11][C@@H:10]([OH:9])[CH2:34][CH2:33]2)[CH2:13][CH2:14]3)[CH2:17][CH2:18]1)[CH3:27])[CH3:25]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 251110Cholestanol benzoate

생성물 1

HCID 6665Dihydrocholesterol수율 76%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of pyridazine 12 (113 mg, 0.22 mmol) in THF (1 mL) and MeOH (2 mL) was treated with 1M NaOH (0.29 mL, 0.29 mmol) and allowed to stand at ambient temperature for 16 h. The solvent was evaporated at reduced pressure and the residue was treated with CH2Cl2 (50 mL) and a 10% Na2CO3 solution (20 mL). The organic layer was separated, dried over MgSO4, filtered, and evaporated to dryness. The residue was purified by flash chromatography on 4 g of silica gel 60 using MeOH/CHCl3 (5:95) giving 65 mg (72%) of 13, which crystallized from CH2Cl2 /acetone, mp 203°-205° C. 1H NMR: δ3.71 (m, 1H), 3.13 (dd, 1H, J=5.6, 13.4 Hz), 3.10 (dd, 1H, J=6.8, 16.5 Hz), 2.95 (dd, 1H, J=10.6, 16.3 Hz), 2.61 (dd, 1H, J=12.8, 17.9 Hz), 2.27 (dd, 1H, J=6.1, 11.0 Hz), 2.23 (ddd, 1H, J=3.6, 3.6, 13.4 Hz), 1.06 (s, 3H), 0.99 (d, 3H, J=6.2 Hz), 0.89 (d, 6H, J=6.6 Hz), 0.80 (s, 3H). IR (Nujol): 3301, 1626, 1554, 1035 cm-1. EIMS (m/z): 410 (M+), 395 (M-Me). Anal. (C27H42N2O): C, H, N.

후처리

  1. customThe solvent was evaporated at reduced pressure
  2. additionthe residue was treated with CH2Cl2 (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on 4 g of silica gel 60 using MeOH/CHCl3 (5:95)

출처 및 근거

ORD 기록
ord-897d3c4b38d14067be4826b8f6627324
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05510340

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