Triphenylphosphine → HCID 69815698, compound

HRID 902641Notes

Reaction equation

HRID 902641 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:19][C:20]1[C:45]([C:46]([F:49])([F:48])[F:47])=[CH:44][CH:43]=[CH:42][C:21]=1[CH2:22][N:23]([CH2:28][CH:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:26][CH2:25][CH2:24][N:23]([CH2:22][C:21]3[CH:42]=[CH:43][CH:44]=[C:45]([C:46]([F:47])([F:48])[F:49])[C:20]=3[Cl:19])[CH2:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:13]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 12523464HCID 12523464, compoundHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

Product 1

HCID 69815698HCID 69815698, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 1-(3-hydroxyphenyl)-piperidine-4-carboxylic acid ethyl ester (0.19 g, 0.77 mmol) in 10 mL of anhydrous toluene was added 3-[(2-chloro-3-(trifluoromethyl)-benzyl)-(2,2-diphenyl-ethyl)-amino]-propan-1-ol (0.41 g, 0.92 mmol). Polymer bound triphenyphosphine (0.41 g, 1,23 mmol, 3 mmol/g, Fluka Chemie) was then added, and the mixture was reacted for 15 minutes. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate (0.2 g, 0.96 mmol) was added in a dropwise fashion. After stirring at RT overnight, the crude reaction mixture was filtered and the solid was washed with EtOAc. After concentration of the filtrate in vacuo, the crude product was purified by column chromatography over silica gel (silica gel 60, EM Science) using 10% EtOAc: hexane as eluent to afford 0.32 g (62%) of the title compound as an oil: MS(ESI) 679.0 (M+H+).

Workup

  1. additionwas then added
  2. customthe mixture was reacted for 15 minutes
  3. customthe crude reaction mixture
  4. filtrationwas filtered
  5. washthe solid was washed with EtOAc
  6. customAfter concentration of the filtrate in vacuo, the crude product was purified by column chromatography over silica gel (silica gel 60, EM Science)

Sources & evidence

ORD record
ord-3bf139a94f06467291238ffc0d8a5712
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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