Sodium hydride → HCID 137331243, compound

HRID 2105414Notes

Reaction equation

HRID 2105414 reaction equation
[CH3:1][SiH:2]([CH3:35])[O:3][CH:4]([C:29]([CH3:34])([CH3:33])[CH:30]([CH3:32])[CH3:31])[C@H:5]1[N:10]2[C:11]3[CH:12]=[CH:13][C:14]([O:18][CH:19]4[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]4)=[CH:15][C:16]=3[CH:17]=[C:9]2[C:8](=[O:28])[NH:7][CH2:6]1.[H-].[Na+].Br[CH2:39][CH:40]1[CH2:42][CH2:41]1>>[CH:40]1([CH2:39][N:7]2[CH2:6][C@@H:5]([CH:4]([C:29]([CH3:33])([CH3:34])[CH:30]([CH3:31])[CH3:32])[O:3][SiH:2]([CH3:1])[CH3:35])[N:10]3[C:11]4[CH:12]=[CH:13][C:14]([O:18][CH:19]5[CH2:24][CH2:23][N:22]([CH:25]([CH3:26])[CH3:27])[CH2:21][CH2:20]5)=[CH:15][C:16]=4[CH:17]=[C:9]3[C:8]2=[O:28])[CH2:42][CH2:41]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 137331242HCID 137331242, compound

Product 1

HCID 137331243HCID 137331243, compoundYield 38%

Procedure

The title compound was synthesized in analogy to example 17, from (S)-4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-8-(1-isopropyl-piperidin-4-yloxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 12, intermediate a)), sodium hydride and 1-(bromomethyl)cyclopropane, to give the desired product as a colorless oil (38%).

Sources & evidence

ORD record
ord-2fabfea467c0485eadd1c060c042abfc
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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