Diethyl Ether → 3alpha-Nicotinoyloxy-5alpha-pregnan-20-one

HRID 232804

反応式

HRID 232804 の反応式
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1.CCOCC>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:25]([O:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 92786Allopregnanolone

生成物 1

HCID 544380323alpha-Nicotinoyloxy-5alpha-pregnan-20-one収率 96%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
90 °C

実験手順

To 3α-hydroxy-5α-pregnan-20-one (464 mg, 318.5 g/m, 1.5 mmol) and 4-dimethylaminopyridine (DMAP, 195 mg, 122.17 g/m, 1.6 mmol) dissolved in 10 mL of dry pyridine was added nicotinoyl chloride hydrochloride (285 mg, 178.02 g/m, 1.6 mmol). The reaction mixture was heated at 90° C. for 5 hours and poured into 300 mL of ether. The organic layer was washed twice with saturated sodium bicarbonate, twice with water, dried over magnesium sulfate, and concentrated in vacuo to give the crude product. The crude material was filtered through a bed of silica gel using hexane/ethyl acetate (50:50) elution. The first two fractions gave the title compound (604 mg, 421 6/m, 1.43 mmol, 96%).

後処理

  1. washThe organic layer was washed twice with saturated sodium bicarbonate, twice with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give the crude product
  5. filtrationThe crude material was filtered through a bed of silica gel
  6. washhexane/ethyl acetate (50:50) elution

出典と根拠

ORDレコード
ord-0d00213721f34e9290417906754dafe7
出典データセット
uspto-grants-1997_01
特許番号
US05591733

関連ノート

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