Triphenylphosphine → 2-[2-(7-Chloro-6-nitro-2-oxo-3-thiophen-2-yl-1,2-dihydro-quinolin-4-yloxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1275591Notes

Reaction equation

HRID 1275591 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[C:7]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[CH2:35][CH2:36]O)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[CH2:35][CH2:36][O:18][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([N+:19]([O-:21])=[O:20])[CH:4]=2)[NH:9][C:8](=[O:12])[C:7]=1[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 547119717-chloro-4-hydroxy-6-nitro-3-(thiophen-2-yl)quinolin-2(1H)-one

Product 1

HCID 536939232-[2-(7-Chloro-6-nitro-2-oxo-3-thiophen-2-yl-1,2-dihydro-quinolin-4-yloxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl esterYield 53.2%

Procedure

To a solution of 7-chloro-4-hydroxy-6-nitro-3-thiophen-2-yl-1H-quinolin-2-one (50 mg in 2.5 mL of tetrahydrofuran) at 0° C. was added 44 mg of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid tert-butyl ester and 63 mg of triphenylphosphine followed by 0.04 mL of diethyl azodicarboxylate and the mixture warmed to room temperature. After 24 hours, the solvents were removed in vacuo and the residue purified by flash chromatography on silica gel (hexane:ethyl acetate, 90:10; then 80:20; then 60:40) to give the title compound (44 mg).

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue purified by flash chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-3631a6205f9f4aea8c9746be87505462
Source dataset
uspto-grants-2000_12
Patent number
US06162813

Reaction notes

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