Tetrahydrofuran → HCID 90403375, compound

HRID 1049289Notes

Reaction equation

HRID 1049289 reaction equation
[CH2:1]1[C:4]2([CH2:7][CH2:6][CH2:5]2)[CH2:3][CH:2]1[C:8]([OH:10])=O.C(Cl)(=O)C(Cl)=O.[NH4+:17].[OH-].C1COCC1>C(Cl)Cl.CN(C=O)C.O>[CH2:1]1[C:4]2([CH2:7][CH2:6][CH2:5]2)[CH2:3][CH:2]1[C:8]([NH2:17])=[O:10]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 20320775Spiro[3.3]heptane-2-carboxylic acid

Product 1

HCID 90403375HCID 90403375, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of spiro[3.3]heptane-2-carboxylic acid (0.5 g, 3.57 mmol) in DCM (5 mL) was treated with oxalyl chloride (0.406 mL, 4.64 mmol) and 1 drop of DMF and stirred at RT for 2 h. The mixture was added drop-wise to a mixture of NH4OH (5 mL, 128 mmol) and THF (5 mL) and stirred at RT overnight. The mixture was treated with H2O, the solids removed via filtration, the filtrate saturated with solid NaCl, extracted with 3:1 DCM/THF (3×) and the combined organics were washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford spiro[3.3]heptane-2-carboxamide (440 mg, 89%). 1H NMR (400 MHz, DMSO-d6): δ 7.07 (s, 1H), 6.62 (s, 1H), 2.76 (m, 1H), 2.01 (m, 4H), 1.96 (t, J=7.2 Hz, 2H), 1.80 (m, 2H), 1.76-1.69 (m, 2H).

Workup

  1. additionThe mixture was added drop-wise
  2. stirringstirred at RT overnight
  3. customthe solids removed via filtration
  4. extractionthe filtrate saturated with solid NaCl, extracted with 3:1 DCM/THF (3×)
  5. washthe combined organics were washed with satd
  6. dry with materialNaHCO3, then brine, dried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6437e1f835c742a6ac9b5d7e91d0f285
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

Loading…