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

HRID 1613974노트

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HRID 1613974 반응식
[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]

참가 물질

7

반응물 4

HCID 4311764Sodium borohydride2회HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride2회HCID 86746637Ethyl (20Z)-20-formamido-9alpha-hydroxy-3-methoxypregna-3,5,17(20)-trien-21-oate

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

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온도
5 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-715b762d55a643e2b6f8f84ec819ee10
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05194602

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