Triethylamine → HCID 91421041, compound

HRID 1243151Notes

Reaction equation

HRID 1243151 reaction equation
[C:1]([O:5][C:6]([C:8]1([C:18]([OH:20])=O)[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.P([N:44]=[N+:45]=[N-:46])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O>C1COCC1>[C:1]([O:5][C:6]([C:8]1([C:18]([N:44]=[N+:45]=[N-:46])=[O:20])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 69585111HCID 69585111, compound

Product 1

HCID 91421041HCID 91421041, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dihydro-1H-naphthalene-2,2-dicarboxylic acid tert-butyl ester from Example 43A was dissolved in THF (50 mL) followed by addition of Et3N (5.05 g, 50 mmol) and (PhO)2PON3 (11 g, 40 mmol) at 0° C. After 3 hours the volatiles were removed under reduced pressure and the residue purified by column chromatography to provide the titled compound (13.1 g, 58% over three steps).

Workup

  1. customAfter 3 hours the volatiles were removed under reduced pressure
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-489f44869d3b4e59b51e1442ad013528
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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