(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 → Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

HRID 8745

反应方程式

HRID 8745 反应方程式
[CH2:1]([C:6]1([C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=C.CSC.C[OH:27]>>[O:27]=[CH:4][CH2:3][CH2:2][CH2:1][C:6]1([C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:8][CH2:7]1

参与物

4

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 1068二甲基硫HCID 11232181Methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

产物 1

HCID 86597419Methyl 4-(4-oxobut-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

实验过程

A solution of methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate (29.4 g, 0.0945 mol) from Step B in methanol (1000 mL) was cooled to −78° C. in a dry ice/methanol bath and ozone was bubbled into the solution until a blue color persisted. The excess ozone was removed with a stream of nitrogen and then methyl sulfide (69 mL, 0.95 mol) was added, the cooling bath was removed, and the reaction mixture was allowed to warm to room temperature over 1.5 h. The reaction mixture was then concentrated. The residue was then purified by flash chromatography eluting with 2:1 heptane/ethyl acetate to afford the title compound (23.0 g).

后处理

  1. customozone was bubbled into the solution until a blue color
  2. customThe excess ozone was removed with a stream of nitrogen
  3. customthe cooling bath was removed
  4. concentrationThe reaction mixture was then concentrated
  5. customThe residue was then purified by flash chromatography
  6. washeluting with 2:1 heptane/ethyl acetate

来源与证据

ORD记录
ord-093ff50ed82045c98be5e1147b0de0d3
来源数据集
uspto-grants-2006_08
专利号
US07091211B2

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