Triphenylphosphine → HCID 86674596, compound

HRID 2170712Notes

Reaction equation

HRID 2170712 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[CH:16][CH:17]=3)[C:12]([CH3:25])=[C:11]2[CH3:26])[CH3:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@H:47]([CH3:52])[C:48]([O:50][CH3:51])=[O:49].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:51][O:50][C:48](=[O:49])[C@@H:47]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[CH:16][CH:17]=3)[C:12]([CH3:25])=[C:11]2[CH3:26])[CH3:9])=[CH:6][CH:7]=1)[CH3:52]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 637514(+)-Methyl lactateHCID 5363146Diisopropyl azodicarboxylateHCID 86674595HCID 86674595, compound

Product 1

HCID 86674596HCID 86674596, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To allyl 1-(1-(4-hydroxyphenyl)ethyl)-2,3-dimethyl-1H-indole-5-carboxylate (0.286 g, 0.82 mmol) in THF (0.8 mL) in an ice bath was added triphenylphosphine (0.28 g, 1.07 mmol) and then (R)-methyl 2-hydroxypropanoate (0.093 mL, 0.98 mmol). DIAD (0.24 mL, 1.23 mmol) was added dropwise to the cold solution. The mixture was stirred at room temperature for 16 hr. The solvent was removed and the residue was purified by silica gel chromatography to obtain the title compound. ESI-MS (m/z): 436 [M+H]+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1ddeef3d6a3d4cc9a90064cb899531cc
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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