Triethylamine → 445306-47-8

HRID 1824001Notes

Reaction equation

HRID 1824001 reaction equation
[CH3:1][O:2][C:3]([C:5]1(C(O)=O)[C:7]2([CH2:9][CH2:8]2)[CH2:6]1)=[O:4].C1C=CC(P([N:27]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.CCN(CC)CC.[ClH:37].O1CCOCC1>CC(O)(C)C>[ClH:37].[CH3:1][O:2][C:3]([C:5]1([NH2:27])[C:7]2([CH2:9][CH2:8]2)[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 10773458HCID 10773458, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 67031096445306-47-8Yield 20%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a mixture of spiro[2.2]pentane-1,1-dicarboxylic acid methyl ester (400 mg, 2.30 mmol) in 3 mL of anhydrous t-BuOH was added 700 mg (2.50 mmol) of DPPA and 278 mg (2.70 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 82 mg (20%) of 1-amino-spiro[2.2]pentane-1-carboxylic acid methyl ester hydrochloride salt as a white solid. 1H NMR (300 MHz, CDCl3) δ 9.19 (br s, 3 H), 3.81 (s, 3 H), 2.16, (d, J=5.5 Hz, 1 H), 2.01 (d, J=5.5 Hz, 1 H), 1.49 (m, 1 H), 1.24, (m, 1 H), 1.12 (m, 2 H). LRMS of free amine: MS m/z 142 (M++1). Section 2 of Example 12 The following P1′ intermediates were prepared as described: 1. Preparation of Cyclopropylsulfonamide (Alternate Route):

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

Sources & evidence

ORD record
ord-76d3327f506b4fb68830e3956057ae26
Source dataset
uspto-grants-2006_05
Patent number
US07041698B2

Reaction notes

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