Phenol → (S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylate

HRID 2259205Notes

Reaction equation

HRID 2259205 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]1(O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 996PhenolHCID 643448(S)-(-)-N-Boc-prolinolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 10636271(S)-tert-Butyl 2-(phenoxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2.01 g (10 mmol) sample of (S)-1-BOC-2-pyrrolidinemethanol (from Example 1a) and 1.41 g (15 mmol) of phenol (Aldrich) were added to a complex of TPP and DEAD, (prepared as in Example 5b above, 15 mmol of each) in 100 mL of THF. The reaction was stirred for 16 hr, the solvents were removed under vacuum, and the residue was extracted with hexane and chromatographed on silica gel to give 0.7 g of the title compound.

Workup

  1. customthe solvents were removed under vacuum
  2. extractionthe residue was extracted with hexane
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-333d2d75ed2c48cf8ae9c12738f211c8
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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