Triphenylphosphine → HCID 68926331, compound

HRID 1786031Notes

Reaction equation

HRID 1786031 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[CH2:10][OH:11])=[O:4].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]([C@H:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([C:52](=[O:60])[C:53]3[CH:58]=[CH:57][C:56](O)=[CH:55][CH:54]=3)[C@@H:44]([CH3:61])[CH2:43]2)[C:39](=[O:41])[CH3:40])=[CH:34][CH:33]=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[C:39]([N:38]([C:35]1[CH:34]=[CH:33][C:32]([Cl:31])=[CH:37][CH:36]=1)[C@H:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[N:45]([C:52]([C:53]2[CH:58]=[CH:57][C:56]([O:11][CH2:10][CH:6]3[CH2:7][CH2:8][CH2:9][CH:5]3[C:3]([O:2][CH3:1])=[O:4])=[CH:55][CH:54]=2)=[O:60])[C@@H:44]([CH3:61])[CH2:43]1)(=[O:41])[CH3:40]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 24722409Methyl (1R,2R)-2-(hydroxymethyl)cyclopentane-1-carboxylateHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 68926331HCID 68926331, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trans-2-Hydroxymethyl-cyclopentanecarboxylic acid methyl ester (0.127 g, 0.81 mmol) was dissolved in 10 ml toluene at room temperature with PPh3 (0.211 g, 0.81 mmol), then added N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide (0.1 g, 0.23 mmol) and stirred for 5 min. DEAD (0.141 g, 0.81 mmol) was added and the reaction was stirred for 18 h at room temperature. The reaction was concentrated and purified by silica gel chromatography (45% dichloromethane/55% ethyl acetate) to afford methyl 2-[(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)methyl]cyclopentanecarboxylate (0.12 g, 90%).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography (45% dichloromethane/55% ethyl acetate)

Sources & evidence

ORD record
ord-18b6d17178be4e53895593555fe05479
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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