Triphenylphosphine → HCID 11220377, compound

HRID 2414773Notes

Reaction equation

HRID 2414773 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.O[CH:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1.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][CH:16]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15]3)[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 44169391-Boc-3-pyrrolidinol

Product 1

HCID 11220377HCID 11220377, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-hydroxyindole (2.66 g, 20.0 mmol), t-butyl 3-hydroxy-1-pyrrolidinecarboxylate (7.5 g, 40.0 mmol) and triphenylphosphine (φ3P) (10.5 g 40.0 mmol) in THF is treated with diethyl azodicarboxylate (DEAC)(6.3 ml, 40.0 mmol) under nitrogen at room temperature, stirred for 2 h at room temperature and concentrated in vacuo. The resultant residue is stirred under ether, cooled and filtered. The filtercake is washed with cold ether. The filtrates are combined and concentrated in vacuo. The residue is purified by flash chromatography (silica gel, EtOAc/hexane: 2/80) to give the title compound as a white solid, 3.98 g, mp 164-165° C., identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe resultant residue is stirred under ether
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe filtercake is washed with cold ether
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography (silica gel, EtOAc/hexane: 2/80)

Sources & evidence

ORD record
ord-8810c73ef58546ed9632bf8d78c6d202
Source dataset
uspto-grants-2004_11
Patent number
US06815456B2

Reaction notes

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