Bromotrimethylsilane → Bromocriptine

HRID 1195077Notes

Reaction equation

HRID 1195077 reaction equation
[CH3:1][CH:2]([CH2:4][C@@H:5]1[N:14]2[C:15]([C@@:17]([NH:22][C:23]([C@@H:25]3[CH:40]=[C:39]4[C@@H:28]([CH2:29][C:30]5[C:38]6[C:33](=[CH:34][CH:35]=[CH:36][C:37]=64)[NH:32][CH:31]=5)[N:27]([CH3:41])[CH2:26]3)=[O:24])([CH:19]([CH3:21])[CH3:20])[O:18][C@@:13]2([OH:42])[C@H:12]2[N:8]([CH2:9][CH2:10][CH2:11]2)[C:6]1=[O:7])=[O:16])[CH3:3].OP(O)(O)=O.C[Si](C)(C)[Br:50]>ClCCl>[CH3:3][CH:2]([CH2:4][C@@H:5]1[N:14]2[C:15]([C@@:17]([NH:22][C:23]([C@@H:25]3[CH:40]=[C:39]4[C@@H:28]([CH2:29][C:30]5[C:38]6[C:33](=[CH:34][CH:35]=[CH:36][C:37]=64)[NH:32][C:31]=5[Br:50])[N:27]([CH3:41])[CH2:26]3)=[O:24])([CH:19]([CH3:20])[CH3:21])[O:18][C@@:13]2([OH:42])[C@H:12]2[N:8]([CH2:9][CH2:10][CH2:11]2)[C:6]1=[O:7])=[O:16])[CH3:1]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 1230977655852-82-9

Product 1

HCID 31101Bromocriptine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the process of Example 30, 1 g of α-ergocryptine phosphate is brominated with 2.0 ml of trimethylbromosilane. After isolating, the title base is obtained in a yield of 0.9 g (0.001359 mole, 91.5%), m.p.: 218° C., [α]D20 =-195° (c=1, dichloromethane).

Workup

  1. customAfter isolating

Sources & evidence

ORD record
ord-fb7ea1fbb60f4e91b6c9cda98e4beac2
Source dataset
uspto-grants-1989_03
Patent number
US04816587

Reaction notes

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