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 1858167Notes

Reaction equation

HRID 1858167 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-f33908aa73e14597b837dc2be8856c51
Source dataset
uspto-grants-2000_11
Patent number
US06150522

Reaction notes

Loading…