Lithium diisopropylamide → HCID 77879337, compound

HRID 1395279Notes

Reaction equation

[CH2:1]([C:3]12[CH2:17][CH:7]3[NH:8][CH:9]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=41)[CH:4]2[CH2:5][CH:6]3[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[Li].[CH3:32][S:33][CH2:34][CH2:35][CH2:36][C:37](Cl)=[O:38]>>[CH2:1]([C:3]12[CH2:17][CH:7]3[NH:8][CH:9]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=41)[CH:4]2[CH2:5][C:6]3([C:37](=[O:38])[CH2:36][CH2:35][CH2:34][S:33][CH3:32])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:2]

Participants

Reactant 4

HCID 2724682Lithium diisopropylamide

HCID 3028194Lithium

HCID 12880941HCID 12880941, compound

HCID 1373032654473-54-0

Product 1

HCID 77879337HCID 77879337, compound

Procedure

Following a procedure similar to that described in Examples 1 or 2, it is contemplated that reaction of ethyl 5α-ethyl-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate with lithium diisopropylamide, followed by reaction of the resulting lithium salt with γ-methylmercaptobutyryl chloride and treatment of the resulting product with dilute mineral acid affords ethyl 5α-ethyl-3-(γ-methylmercaptobutyryl)-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylate, which, on heating with trimethylammonium formate, affords 6(eq)-ethyl-11(eq)-(6-methylmercapto-3-oxohexyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine.

Workup

additionwith dilute mineral acid

Sources & evidence

ORD record: ord-a53b50f040fb492dad21e64936830c55
Source dataset: uspto-grants-1980_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04202983

Reaction notes

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