Triphenylphosphine → HCID 86697155, compound

HRID 471449Notes

Reaction equation

HRID 471449 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[C:11]([O:15][C:16]([N:18]1[CH2:21][CH:20]([CH2:22]O)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:21][CH:20]([CH2:22][O:9][C:5]2[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[C:3]([CH3:10])[CH:4]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 819704-Bromo-3,5-dimethylphenolHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 86697155HCID 86697155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-3,5-dimethylphenol (3.7 g, 18.16 mmol), 3-hydroxymethylazetidine-1-carboxylic acid tert-butyl ester (commercially available, EP1889836 A1, 3.40 g, 18.16 mmol), di-tert-butylazodicarboxylate (4.6 g, 19.97 mmol) and triphenylphosphine (5.24 g, 19.97 mmol) are suspended in dichloromethane (100 mL) and stirred for 2 hours at room temperature. The solvent is removed under vacuum and the residue suspended in diethyl ether, cooled and the precipitate is filtered off. The solvent is removed under vacuum to give the title compound

Workup

  1. customThe solvent is removed under vacuum
  2. temperaturecooled
  3. filtrationthe precipitate is filtered off
  4. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-a37253335e624a11bd340734d3b8f768
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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