Bromotrimethylsilane → Bromocriptine

HRID 1195079Notes

Reaction equation

HRID 1195079 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 33, 10 g of a mixture of α-ergocryptine phosphate and ergosine phosphate (containing 48.9% of α-ergocryptine base, 1.9% of α-ergocryptinine base, 28.2% of ergosine base and 1.3% of ergosinine base) is brominated with 20 ml of trimethylbromosilane and the title compound is isolated in a yield of 4.7 g (0.007243 mole, 85%), m.p.: 218° C. [α]D20 =-195° (c=1, dichloromethane).

Sources & evidence

ORD record
ord-c599ef09e76a4295818d4258ffb3a092
Source dataset
uspto-grants-1989_03
Patent number
US04816587

Reaction notes

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