Triphenylphosphine → 3-{2-[4-(2,6-Dimethyl-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester

HRID 920566Notes

Reaction equation

HRID 920566 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:25]=1[CH2:26]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:26][C:25]3[C:28]([CH3:32])=[CH:29][CH:30]=[CH:31][C:24]=3[CH3:23])=[CH:19][CH:20]=2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 186748(2,6-Dimethylphenyl)methanolHCID 5363146Diisopropyl azodicarboxylateHCID 666540623-[2-(4-Hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester

Product 1

HCID 670323233-{2-[4-(2,6-Dimethyl-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl esterYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[2-(4-hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester (0.45 g; 1.5 mmol) in THF (10 mL) was added 2,6-dimethylbenzyl alcohol (0.22 g; 1.6 mmol), followed by DIAD (0.43 mL; 2.2 mmol) and triphenylphosphine (0.58 g; 2.2 mmol). The resulting mixture was stirred at RT for 3 days. Subsequently, the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 2:1) to afford 3-{2-[4-(2,6-dimethyl-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester (0.38 g).

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 2:1)

Sources & evidence

ORD record
ord-53ddeb1644a44c129806aafbb14b4531
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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