Tetrahydrofuran → HCID 12132428, compound

HRID 2307396Notes

Reaction equation

HRID 2307396 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[NH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16]O.C1(P([C:31]2[CH:36]=[CH:35]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=N[C:39]([O:41]CC)=[O:40].[CH2:49]1COCC1>>[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH2:16][C@@H:12]3[CH2:13][CH2:14][CH2:15][N:11]3[C:39]([O:41][C:36]([CH3:35])([CH3:31])[CH3:49])=[O:40])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 754211H-indol-4-olHCID 90908ProlinolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 12132428HCID 12132428, compound

Procedure

A solution of 4-hydroxyindole (1.33 g, 10.0 mmol), (S)-(−)-1-t-butoxycarbonyl)-2-pyrrolidine methanol (4.02 g, 20.0 mmol) and triphenylphosphine (5.3 g, 20.0 mmol) in THF is treated with diethyl azodicarboxylate (3.2 ML, 20.0 mmol) under nitrogen at room temperature, stirred for 2 h at room temperature and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 20/80) to give the title compound as a white solid, 1.5 g, mp 40-41° C., identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 20/80)

Sources & evidence

ORD record
ord-813be9f1938e4c76943440f47ba6527f
Source dataset
uspto-grants-2004_12
Patent number
US06831094B2

Reaction notes

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