Sodium borohydride → (20Z)-20-Formamido-3-methoxypregna-3,5,17(20)-triene-9alpha,21-diol

HRID 1613974ノート

反応式

HRID 1613974 の反応式
[BH4-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:9]([NH:11]/[C:12](=[C:18]1/[CH2:19][CH2:20][C@@H:21]2[C@:35]/1([CH3:36])[CH2:34][CH2:33][C@@:32]1([OH:37])[C@H:22]2[CH2:23][CH:24]=[C:25]2[C@:30]1([CH3:31])[CH2:29][CH2:28][C:27]([O:38][CH3:39])=[CH:26]2)/[C:13](OCC)=[O:14])=[O:10].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1.C(O)C>[CH:9]([NH:11]/[C:12](=[C:18]1/[CH2:19][CH2:20][C@@H:21]2[C@:35]/1([CH3:36])[CH2:34][CH2:33][C@@:32]1([OH:37])[C@H:22]2[CH2:23][CH:24]=[C:25]2[C@:30]1([CH3:31])[CH2:29][CH2:28][C:27]([O:38][CH3:39])=[CH:26]2)/[CH2:13][OH:14])=[O:10]

参加物

7

反応物 4

HCID 4311764Sodium borohydride2 回HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride2 回HCID 86746637Ethyl (20Z)-20-formamido-9alpha-hydroxy-3-methoxypregna-3,5,17(20)-trien-21-oate

生成物 1

HCID 86746638(20Z)-20-Formamido-3-methoxypregna-3,5,17(20)-triene-9alpha,21-diol収率 24.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

Under a nitrogen atmosphere sodium borohydride (0.53 g) and lithium aluminium hydride (0.65 g) were added to a stirred solution of ethyl (20Z)-20-formamido-9α-hydroxy-3-methoxypregna-3,5,17(20)-trien-21-oate (4.85 g, prepared according to example 10), in dry tetrahydrofuran (100 ml) at 0° C. The reaction mixture was stirred at 5° C. for 2 hours, after which another 0.54 g of sodium borohydride and 0.65 g of lithium aluminium hydride were added. Stirring was continued at 5° C. for 1.5 hours, then ethanol (50 ml) was added dropwise to decompose excess reducing agent. After adding 60 ml of an aqueous solution of sodium potassium tartrate, the reaction mixture was filtered and extracted with ethyl acetate. The organic phase was washed with an aqueous sodium carbonate solution and with water, dried (MgSO4) and concentrated under reduced pressure. The residue (3.02 g) was purified by column chromatography (toluene/acetone 2/1 containing 0,1% triethylamine) to provide 1.08 g of the title compound.

後処理

  1. stirringStirring
  2. waitwas continued at 5° C. for 1.5 hours
  3. filtrationthe reaction mixture was filtered
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with an aqueous sodium carbonate solution and with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue (3.02 g) was purified by column chromatography (toluene/acetone 2/1 containing 0,1% triethylamine)

出典と根拠

ORDレコード
ord-715b762d55a643e2b6f8f84ec819ee10
出典データセット
uspto-grants-1993_03
特許番号
US05194602

反応ノート

読み込み中…