Hydrochloric Acid → 1-Azaspiro(4.5)-decane-2,8-dione

HRID 1257642Notes

Reaction equation

HRID 1257642 reaction equation
O1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][C:10](=[O:13])[NH:9]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1>[NH:9]1[C:8]2([CH2:14][CH2:15][C:5](=[O:4])[CH2:6][CH2:7]2)[CH2:12][CH2:11][C:10]1=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 111834371,4-Dioxa-9-azadispiro[4.2.4.2]tetradecan-10-one

Product 1

HCID 114125941-Azaspiro(4.5)-decane-2,8-dioneYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1,4-dioxa-9-aza-dispiro[4.2.4.2]tetradecan-10-one (prepared according to J. Org. Chem. 2004, 69, 2755) (500 mg, 2.4 mmol) in THF (7 mL) was treated with 1M aqueous HCl (7 mL) and the resulting mixture stirred at ambient temperature for 20 hours. The reaction mixture was quenched with 1M aqueous NaOH (7 mL) and the mixture concentrated under vacuum. The resulting solid was purified by column chromatography on silica gel (gradient: DCM then 2 to 10% methanol in ethyl acetate) to afford 398 mg (quant.) of 1-aza-spiro[4.5]decane-2,8-dione. LCMS (Method B, ESI): RT=1.63 min, 168; 1H NMR (400 MHz, CDCl3) δ: 3.95 (s, 1H), 3.77-3.71 (m, 1H), 2.46-2.44 (m, 3H), 2.05-2.03 (m, 3H), 1.81-1.65 (m, 4H).

Workup

  1. customThe reaction mixture was quenched with 1M aqueous NaOH (7 mL)
  2. concentrationthe mixture concentrated under vacuum
  3. customThe resulting solid was purified by column chromatography on silica gel (gradient

Sources & evidence

ORD record
ord-1ccecc070f08471aa5d3e74aaf67a9f1
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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