3-Nitrophenol → HCID 58154811, compound

HRID 2359409Notes

Reaction equation

HRID 2359409 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O: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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH:16]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 111373-NitrophenolHCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 58154811HCID 58154811, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-nitrophenol (4.0 g, 28.8 mmol), tert-butyl 3-hydroxypyrrolidine-1-carboxylate (5.94 g, 31.7 mmol), PPh3 (8.3 g, 31.7 mmol) in THF (40 mL) at 0° C. over argon was added DEAD (5.52 g, 31.7 mmol). The reaction was warmed to room temperature and stirred for 18 hours. The reaction mixture was concentrated and purified by column chromatography to obtain tert-butyl 3-(3-nitrophenoxy)pyrrolidine-1-carboxylate (8.73 g, 98% yield)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-996ed216f3a340dfb2d75a8bf2b88531
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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