Bromotrimethylsilane → HCID 13059865, compound

HRID 1195074Notes

Reaction equation

HRID 1195074 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH:20]=[C:19]2[C@@H:9]([CH2:10][C:11]3[C:21]4[C:14](=[CH:15][CH:16]=[CH:17][C:18]2=4)[NH:13][CH:12]=3)[N:7]([CH3:8])[CH2:6]1)=[O:4].C[Si](C)(C)[Br:24]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH:20]=[C:19]2[C@@H:9]([CH2:10][C:11]3[C:21]4[C:14](=[CH:15][CH:16]=[CH:17][C:18]2=4)[NH:13][C:12]=3[Br:24])[N:7]([CH3:8])[CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 76113BromotrimethylsilaneHCID 11414860D-Lysergic acid methyl ester

Product 1

HCID 13059865HCID 13059865, compound

Procedure

Following the process of Example 25, 1 g of lysergic acid methyl ester is reacted with 2.7 ml of trimethylbromosilane and the product is purified by chromatography on a Kieselgel column by using a 7:3 mixture of benzene and acetone as eluant. After recrystallization from benzene, the title compound is obtained in a yield of 0.7 g (0.0019 mole, 55%), m.p.: 177°-178° C., [α]D20 =+41° (c=1, chloroform).

Workup

  1. customthe product is purified by chromatography on a Kieselgel column
  2. additiona 7:3 mixture of benzene and acetone as eluant
  3. customAfter recrystallization from benzene

Sources & evidence

ORD record
ord-826796b63d134021abb4dbdf9578747a
Source dataset
uspto-grants-1989_03
Patent number
US04816587

Reaction notes

Loading…