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

HRID 232804

반응식

HRID 232804 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 544380323alpha-Nicotinoyloxy-5alpha-pregnan-20-one수율 96%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

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온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0d00213721f34e9290417906754dafe7
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591733

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