spiro[3.3]heptane-2,2-dicarboxylic acid → Spiro[3.3]heptane-2-carboxylic acid

HRID 1049288Notes

Reaction equation

HRID 1049288 reaction equation
[CH2:1]1[C:4]2([CH2:7][CH2:6][CH2:5]2)[CH2:3][C:2]1(C(O)=O)[C:8]([OH:10])=[O:9]>N1C=CC=CC=1>[CH2:1]1[C:4]2([CH2:7][CH2:6][CH2:5]2)[CH2:3][CH:2]1[C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 271511spiro[3.3]heptane-2,2-dicarboxylic acid

Product 1

HCID 20320775Spiro[3.3]heptane-2-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of spiro[3.3]heptane-2,2-dicarboxylic acid (1.737 g, 9.43 mmol) in pyridine (20 mL) was heated at 115° C. overnight, cooled to RT and concentrated to dryness. The residue was treated with 6M HCL, extracted with DCM (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford spiro[3.3]heptane-2-carboxylic acid (1.21 g, 92%). 1H NMR (400 MHz, DMSO-d6): δ 11.98 (s, 1H), 2.85 (m, 1H), 2.15-2.03 (m, 4H), 1.96 (t, J=7.3 Hz, 2H), 1.84 (t, J=7.3 Hz, 2H), 1.76-1.70 (m, 2H).

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue was treated with 6M HCL
  3. extractionextracted with DCM (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-31c3e2e98cd44467899f028d14290818
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

Loading…