Triphenylphosphine → HCID 68925273, compound

HRID 1786053Notes

Reaction equation

HRID 1786053 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]([C@H:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[N:50]([C:57](=[O:65])[C:58]3[CH:63]=[CH:62][C:61](O)=[CH:60][CH:59]=3)[C@@H:49]([CH3:66])[CH2:48]2)[C:44](=[O:46])[CH3:45])=[CH:39][CH:38]=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:61]2[CH:60]=[CH:59][C:58]([C:57]([N:50]3[C:51]4[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=4)[C@H:47]([N:43]([C:44](=[O:46])[CH3:45])[C:40]4[CH:41]=[CH:42][C:37]([Cl:36])=[CH:38][CH:39]=4)[CH2:48][C@@H:49]3[CH3:66])=[O:65])=[CH:63][CH:62]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 5462977Diethyl azodicarboxylateHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

Product 1

HCID 68925273HCID 68925273, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(2-Hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (0.119 g, 0.52 mmol) was dissolved in toluene at room temperature with PPh3 (0.136 g, 0.52 mmol), then added (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.150 g, 0.35 mmol) and stirred for 5 min. DEAD (0.090 g, 0.52 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% CH2Cl2 /55% EtOAc) to afford (2S,4R)-4-[2-(4-{4-[acetyl(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (0.2 g, 90%)

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography (45% CH2Cl2 /55% EtOAc)

Sources & evidence

ORD record
ord-84c8442227934d18a3910544430738a3
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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