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

HRID 504277Notes

Reaction equation

HRID 504277 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-d8007feb9b754b52afc0f0e34a1dd4b6
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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