Allyl bromide → Rocuronium Bromide

HRID 329958

Reaction equation

HRID 329958 reaction equation
[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]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 16064933(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Product 1

HCID 441351Rocuronium Bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-59c713a0ac23449fae6d5f1de6019272
Source dataset
uspto-grants-1990_01
Patent number
US04894369

Linked notes

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