3-溴丙烯 → Rocuronium Bromide

HRID 329958

反应方程式

HRID 329958 反应方程式
[CH2:1]([Br:4])[CH:2]=[CH2:3].[C:5]([O:8][C@H:9]1[C@@H:14]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:13][C@H:12]2[C@H:20]3[C@H:30]([CH2:31][CH2:32][C@:10]12[CH3:11])[C@:28]1([CH3:29])[C@H:23]([CH2:24][C@H:25]([OH:39])[C@@H:26]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH2:27]1)[CH2:22][CH2:21]3)(=[O:7])[CH3:6]>ClCCl>[Br-:4].[C:5]([O:8][C@H:9]1[C@@H:14]([N+:15]2([CH2:3][CH:2]=[CH2:1])[CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:13][C@H:12]2[C@H:20]3[C@H:30]([CH2:31][CH2:32][C@:10]12[CH3:11])[C@:28]1([CH3:29])[C@H:23]([CH2:24][C@H:25]([OH:39])[C@@H:26]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[CH2:27]1)[CH2:22][CH2:21]3)(=[O:7])[CH3:6]

参与物

4

反应物 2

HCID 78413-溴丙烯HCID 160649333Α,17Β-(二羟基)-2Β-(吗啉-1-基)-16-(吡咯烷-1-基)-5Α-雄甾-17-乙酸酯

产物 1

HCID 441351Rocuronium Bromide

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

2-propenyl bromide (1.95 ml) was added to a solution of (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16(1-pyrrolidinyl)-androstane-3,17-diol 17-acetate (1.35 g) in dichloromethane (27 ml) and the solution was sealed in a pressure bottle at room temperature for 22 h. The solvent was removed under reduced pressure with the minimum of heating and the crude solid (1.59 g) was chromatographed on alumina (Fluka type 5016A). The pure fractions were combined, taken up in dichloromethane (15 ml) and diethyl ether (100 ml) was added to precipitate pure 1-[(2β,3α,5α,16β,17β)-17-acetyloxy-3-hydroxy-2-(4-morpholinyl)-androstan-16-yl]-1-(2propenyl)-pyrrolidinium bromide (1.14 g), m.p. 161°-169° C.; [α]D20 =+18.7° (c 1.03 in CHCl3).

后处理

  1. customthe solution was sealed in a pressure bottle at room temperature for 22 h
  2. customThe solvent was removed under reduced pressure with the minimum
  3. temperatureof heating
  4. customthe crude solid (1.59 g) was chromatographed on alumina (Fluka type 5016A)
  5. additiondiethyl ether (100 ml) was added
  6. customto precipitate pure 1-[(2β,3α,5α,16β,17β)-17-acetyloxy-3-hydroxy-2-(4-morpholinyl)-androstan-16-yl]-1-(2propenyl)-pyrrolidinium bromide (1.14 g), m.p. 161°-169° C.
  7. custom[α]D20 =+18.7° (c 1.03 in CHCl3)

来源与证据

ORD记录
ord-59c713a0ac23449fae6d5f1de6019272
来源数据集
uspto-grants-1990_01
专利号
US04894369

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