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

HRID 2275532Notes

Reaction equation

HRID 2275532 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-e17a5900031c46d88d7e6c3eedea3189
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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