Triethylamine → HCID 67031170, compound

HRID 720239Notes

Reaction equation

HRID 720239 reaction equation
[CH3:1][O:2][C:3]([C:5]1(C(O)=O)[C:7]2([CH2:10][CH2:9][CH2:8]2)[CH2:6]1)=[O:4].C1C=CC(P([N:28]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.CCN(CC)CC.[ClH:38].O1CCOCC1>CC(O)(C)C>[ClH:38].[CH3:1][O:2][C:3]([C:5]1([NH2:28])[C:7]2([CH2:10][CH2:9][CH2:8]2)[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 204431481,4-Dioxane hydrochlorideHCID 20767963445306-40-1

Product 1

HCID 67031170HCID 67031170, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a mixture of spiro[2,3]hexane-1,1-dicarboxylic acid methyl ester (660 mg, 3.58 mmol) in 3 mL of anhydrous t-BuOH was added 1.08 g (3.92 mmol) of DPPA and 440 mg (4.35 mmol) of Et3N. The mixture was heated at reflux for 21 h and then partitioned between H2O and ether. The ether phase was dried over magnesium sulfate, filtered and concentrated in vacuo to yield an oil. To this oil was added 3 mL of a 4 M HCl/dioxane solution. This acidic solution was stirred at rt for 2 h and then concentrated in vacuo. The residue was triturated with ether to give 400 mg (58%) of desried prodict as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 8.96 (br s, 3H), 3.71 (s, 3H), 2.41 (m, 1H), 2.12 (m, 4H), 1.93 (m, 1H), 1.56 (q, 2H, J=8 Hz). LC-MS of free amine: MS m/z 156 (M++1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 21 h
  3. custompartitioned between H2O and ether
  4. dry with materialThe ether phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield an oil
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether
  10. customto give 400 mg (58%) of desried prodict as a white solid

Sources & evidence

ORD record
ord-7d9f0c5c8ceb4022ac1d9700b4384141
Source dataset
uspto-grants-2006_11
Patent number
US07135462B2

Reaction notes

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