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

HRID 582520ノート

反応式

HRID 582520 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 699056963alpha-Isobutyryloxy-17beta-methoxy-5beta-androstane収率 86.1%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
7.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d0bf7c70a06c4727b271e5fb1610ad85
出典データセット
uspto-grants-1999_07
特許番号
US05925630

反応ノート

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