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

HRID 1647642ノート

反応式

HRID 1647642 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-cbae3cf7c8494d35a3c185b5b209c0c5
出典データセット
uspto-grants-1995_07
特許番号
US05432169

反応ノート

読み込み中…