Triphenylphosphine → HCID 12132432, compound

HRID 2307398Notes

Reaction equation

HRID 2307398 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.[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@@H:19]1[CH2:23]O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH2:23][C@H:19]3[CH2:20][CH2:21][CH2:22][N:18]3[C:16]([O:15][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:17])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 754211H-indol-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

Product 1

HCID 12132432HCID 12132432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-hydroxyindole (1.33 g, 10.0 mmol), (R)-(+)-1-(t-butoxycarbonyl)-2-pyrrolidinemethanol (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 mmol), stirred for 3 h at room temperature and concentrated in vacuo. The resultant residue is treated with EtOAc and filtered through a pad of silica gel. The filtrate is concentrated to give a residue which is purified by chromatography (silica gel, EtOAc:hexanes, 15:80) to afford the title compound as a white solid, 1.08 g, mp 146-147° C.; identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe resultant residue is treated with EtOAc
  3. filtrationfiltered through a pad of silica gel
  4. concentrationThe filtrate is concentrated
  5. customto give a residue which
  6. customis purified by chromatography (silica gel, EtOAc:hexanes, 15:80)

Sources & evidence

ORD record
ord-5155973d107241b1ab8b6ce493628228
Source dataset
uspto-grants-2004_12
Patent number
US06831094B2

Reaction notes

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