6-Methoxynaphthalene-1,2-dione → Tert-butyl 4-hydroxy-4-{[(7-methoxy-3,4-dioxo-3,4-dihydronaphthalen-1-yl)thio]methyl}piperidine-1-carboxylate

HRID 1665273Notes

Reaction equation

HRID 1665273 reaction equation
[OH:1][C:2]1([CH2:15][SH:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[C:24](=[O:30])[CH:23]=[CH:22]2>C(#N)C>[OH:1][C:2]1([CH2:15][S:16][C:22]2[C:21]3[C:26](=[CH:27][CH:28]=[C:19]([O:18][CH3:17])[CH:20]=3)[C:25](=[O:29])[C:24](=[O:30])[CH:23]=2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 137770616-Methoxynaphthalene-1,2-dioneHCID 53438219Tert-butyl 4-hydroxy-4-(mercaptomethyl)piperidine-1-carboxylate

Product 1

HCID 67439043Tert-butyl 4-hydroxy-4-{[(7-methoxy-3,4-dioxo-3,4-dihydronaphthalen-1-yl)thio]methyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-butyl 4-hydroxy-4-{[(7-methoxy-3,4-dioxo-3,4-dihydronaphthalen-1-yl)thio]methyl}piperidine-1-carboxylate was synthesized using tert-butyl 4-hydroxy-4-(mercaptomethyl)piperidine-1-carboxylate, 6-methoxynaphthalene-1,2-dione, acetonitrile as the solvent and conditions outlined in procedure F [step (i)]. The crude intermediate was used in step (ii) without any further purification.

Workup

  1. customThe crude intermediate was used in step (ii) without any further purification

Sources & evidence

ORD record
ord-826761078ef041aa93cb837335488809
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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