(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮 → (1R,4S)-rel-4-(Acetylamino)-2-cyclopentene-1-carboxylic Acid Methyl Ester

HRID 851237

反应方程式

HRID 851237 反应方程式
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.Cl.N[C@@H]1C[C@H:14]([C:16]([OH:18])=O)C=C1.[CH3:19][OH:20]>C(OC(=O)C)(=O)C.N1C=CC=CC=1>[CH3:19][O:20][C:3]([C@H:4]1[CH2:7][C@@H:1]([NH:2][C:16](=[O:18])[CH3:14])[CH:6]=[CH:5]1)=[O:8]

参与物

5

反应物 3

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮HCID 5486782-氮杂双环[2.2.1]庚-5-烯-3-酮HCID 44828817(1S,4R)-4-氨基环戊-2-烯羧酸盐酸盐

产物 1

HCID 361509(1R,4S)-rel-4-(Acetylamino)-2-cyclopentene-1-carboxylic Acid Methyl Ester

试剂、催化剂与溶剂 1

HCID 22348678Acetic anhydride pyridine溶剂

实验过程

Acidic hydrolysis of 2-azabicyclo[2.2.1]hept-5-en-3-one (1, referring to the corresponding number on the flow sheet) to cis-4-aminocyclopent-2-ene carboxylic acid hydrochloride, followed by esterification of the carboxyl function in refluxing methanol and subsequent acetylation of the amino group in acetic anhydride-pyridine, gives methyl-cis-4-acetamidocyclopent-2-ene carboxylate (2). Reduction of the methyl ester of 2 gives, after acetylation, acetate 3. Epoxidation of acetate 3 is stereoselective due to the syn-directing allylic amide group, giving only the cis-epoxide 4. Hydrolysis of the epoxide 4 and subsequent acetylation gives a mixture of 5, 6 and 6a.

来源与证据

ORD记录
ord-841c6861a0c148949ec2508d2f25a3b3
来源数据集
uspto-grants-1983_05
专利号
US04383114

关联笔记

加载中…