Isobutyryl chloride → 3alpha-Isobutyryloxy-17beta-methoxy-5beta-androstane

HRID 582520노트

반응식

HRID 582520 반응식
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[O:21][CH3:22])[CH2:3]1.[C:23](Cl)(=[O:27])[CH:24]([CH3:26])[CH3:25]>N1C=CC=CC=1.C(Cl)Cl>[C:23]([O:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[O:21][CH3:22])[CH2:3]1)(=[O:27])[CH:24]([CH3:26])[CH3:25]

참가 물질

5

반응물 2

HCID 62325Isobutyryl chlorideHCID 128368633alpha-Hydroxy-17beta-methoxy-5beta-androstane

생성물 1

HCID 699056963alpha-Isobutyryloxy-17beta-methoxy-5beta-androstane수율 86.1%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

반응 조건

온도
7.5 °C

실험 절차

A solution of 3α-hydroxy-17β-methoxy-5β-androstane (250 mg, 0.82 mmol) in dry pyridine (2 mL) was treated with isobutyryl chloride (0.12 mL, 1.15 mmol), and N,N-dimethylaminopyridine (5 mg) at 5° C. After stirring the mixture at 5-10° C. for 1 hr the mixture was quenched with HCl solution (0.5N, 25 mL). The mixture was extracted with EtOAc. The organic layer was washed with dil. HCl, water, and brine. After drying over anhyd. MgSO4 the solution was filtered and evaporated to yield the crude product. This crude product was then dissolved in a small amount of CH2Cl2 and poured on a column of silica gel. Elution with hexane:acetone mixture (9:1) gave 3α-isobutyryloxy-17β-methoxy-5β-androstane (266 mg); mp 82-87° C.; TLC Rf (hexane:acetone 9:1)=0.6.

후처리

  1. customwas quenched with HCl solution (0.5N, 25 mL)
  2. extractionThe mixture was extracted with EtOAc
  3. washThe organic layer was washed with dil. HCl, water, and brine
  4. customAfter drying over anhyd
  5. filtrationMgSO4 the solution was filtered
  6. customevaporated
  7. customto yield the crude product
  8. additionpoured on a column of silica gel
  9. washElution with hexane

출처 및 근거

ORD 기록
ord-d0bf7c70a06c4727b271e5fb1610ad85
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925630

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