Imidazole → 3beta-Tert-butyldimethylsilyloxy-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 1647642노트

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HRID 1647642 반응식
[O:1]1[CH:5]=[CH:4][C:3]([C@H:6]2[CH2:11][CH2:10][C@:9]3([OH:26])[C@H:12]4[C@H:22]([CH2:23][CH2:24][C@:7]23[CH3:8])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([OH:25])[CH2:18][CH2:19]2)[CH2:14][CH2:13]4)=[CH:2]1.O1[C@@H]2C[C@H](C3C=COC=3)[C@]3(CC[C@H]4[C@H]([C@@]123)CC[C@H]1[C@]4(C)CC[C@H](O)C1)C.N1C=CN=C1.[Si:58](Cl)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59]>O.CN(C)C=O>[Si:58]([O:25][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:15]([CH2:14][CH2:13][C@@H:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:7]2([CH3:8])[C@:9]3([OH:26])[CH2:10][CH2:11][C@@H:6]2[C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)[CH2:16]1)([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1606964617beta-(3-Furyl)-5beta,14beta-androstane-3beta,14beta-diolHCID 8674878814beta,15beta-Epoxy-17beta(3-furyl)-5beta-androstan-3beta-ol

생성물 1

HCID 700458673beta-Tert-butyldimethylsilyloxy-17beta-(3-furyl)-5beta-androstan-14beta-ol수율 113.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 10 g of 17β-(3-furyl)-5β-androstane-3β,14β-diol (II-a: Ref. comp.) (Minato H. and Nagasaki T., J. Chem. Soc. (C), 1966, 377)in 80 ml of dimethylformamide, 18 g of imidazole and 20.0 g of t-butyldimethylsilyl chloride were added at 0° C. After 12 hrs the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure and 15 g of crude 3β-tert-butyldimethylsilyloxy-17β-(3-furyl)-5β-androstan-14β-ol were obtained. A suspension of this protected alcohol and 1.3 g of KH in 75 ml of tetrahydrofuran was heated at 70° C. for an hr; then 2.7 g of methyl iodide were added. After 30' the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 12 g of 3β-tert-butyldimethylsilyloxy-14β-methoxy-17β-(3-furyl)-5β-androstane as a white amorphous solid.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-cbae3cf7c8494d35a3c185b5b209c0c5
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05432169

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