6-Chloronaphthalene-1,2-dione → Tert-butyl 4-{[(7-chloro-3,4-dioxo-3,4-dihydronaphthalen-1-yl)thio]methyl}-4-hydroxypiperidine-1-carboxylate

HRID 1665271Notes

Reaction equation

HRID 1665271 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.[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[C:23](=[O:29])[CH:22]=[CH:21]2>C(#N)C>[Cl:17][C:18]1[CH:19]=[C:20]2[C:25]([C:24](=[O:28])[C:23](=[O:29])[CH:22]=[C:21]2[S:16][CH2:15][C:2]2([OH:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 203740386-Chloronaphthalene-1,2-dioneHCID 53438219Tert-butyl 4-hydroxy-4-(mercaptomethyl)piperidine-1-carboxylate

Product 1

HCID 67437890Tert-butyl 4-{[(7-chloro-3,4-dioxo-3,4-dihydronaphthalen-1-yl)thio]methyl}-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-butyl 4-{[(7-chloro-3,4-dioxo-3,4-dihydronaphthalen-1-yl)thio]methyl}-4-hydroxypiperidine-1-carboxylate was synthesized using tert-butyl 4-hydroxy-4-(mercaptomethyl)piperidine-1-carboxylate, 6-chloronaphthalene-1,2-dione, acetonitrile as the solvent and conditions outlined in procedure F [step (i)]. The intermediate was purified by flash column chromatography (SiO2, 30% EtOAc in hexanes to 50% EtOAc in hexanes).

Workup

  1. customThe intermediate was purified by flash column chromatography (SiO2, 30% EtOAc in hexanes to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a5dd7c7b3d8d4871abe94b34316ca11a
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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