Triphenylphosphine → 1'-benzyl-3H-spiro[2-benzofuran-1,3'-pyrrolidine]

HRID 557812Notes

Reaction equation

HRID 557812 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([N:20]1[CH2:24][CH2:23][C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][OH:33])(O)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:13]([N:20]1[CH2:24][CH2:23][C:22]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:32][O:33]2)[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 666623191-Benzyl-3-[2-(hydroxymethyl)phenyl]pyrrolidin-3-ol

Product 1

HCID 666617821'-benzyl-3H-spiro[2-benzofuran-1,3'-pyrrolidine]Yield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (4.44 mL, 0.0282 mol) in 1 ml of THF was added to a mixture of 1-benzyl-3-[2-(hydroxymethyl)phenyl]pyrrolidin-3-ol (3.50 g, 0.0124 mol) and triphenylphosphine (7.40 g, 0.0282 mol) in tetrahydrofuran (50 mL, 0.6 mol) at room temperature. The mixture was stirred at room temperature overnight. The reaction solution was concentrated and the residue was flash chromatographed on silica gel column with 50% AcOEt in hexanes to give the desired compound (1.5 g, 46% yield). MS (ESI): 266.1 (M+H+).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customchromatographed on silica gel column with 50% AcOEt in hexanes

Sources & evidence

ORD record
ord-0d5ad5dc0f4541debf46759082463feb
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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