3-Nitrophenol → HCID 54214403, compound

HRID 2259196Notes

Reaction equation

HRID 2259196 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CCC[C@@H]1C(O)=O)(OC(C)(C)C)=O.[N+:30]([C:33]1[CH:34]=[C:35](O)[CH:36]=[CH:37][CH:38]=1)([O-:32])=[O:31].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:37]1[CH:36]=[CH:35][CH:34]=[C:33]([N+:30]([O-:32])=[O:31])[CH:38]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 111373-NitrophenolHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 54214403HCID 54214403, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.5 g (7.46 mmol) sample of (R)-1-t-butoxycarbonyl-2-pyrrolidinemethanol (prepared as in Example 1b above, except starting with the N-BOC-D-proline (Sigma) instead of the N-BOC-L-proline) and 1.56 g (11.19 mmol) of 3-nitrophenol (Aldrich) were added to a complex of TPP and DEAD (prepared as in Example 1 above, 11.2 mmol of each) in 50 mL of THF. The reaction was stirred for 16 hr, the solvents were removed under vacuum, and the residue was chromatographed on silica gel, eluting with 1:1 chloroform:hexane to give 670 mg of the title compound.

Workup

  1. customthe solvents were removed under vacuum
  2. customthe residue was chromatographed on silica gel
  3. washeluting with 1:1 chloroform

Sources & evidence

ORD record
ord-4d8e9ce4d79a40b29c611f7511383d35
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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