Triethylamine → 1-Oxa-3-azaspiro[4.5]decan-2-one

HRID 1724063Notes

Reaction equation

HRID 1724063 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(N(CC)CC)C.N1C=CC=C[C:19]=1[O:24]C(=O)OC1C=CC=CN=1>ClCCl.C(OCC)(=O)C>[O:10]1[C:4]2([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:3][NH:2][C:19]1=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2757370Carbonic acid di-2-pyridyl esterHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)

Product 1

HCID 3490431-Oxa-3-azaspiro[4.5]decan-2-oneYield 74.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Aminomethyl-cyclohexanol hydrogen chloride (250 mg, 1.5 mmol) and triethylamine (0.21 mL, 1.5 mmol) were mixed in dichloromethane (5 mL), and the mixture was stirred for 15 min. Carbonic acid dipyridin-2-yl ester (326 mg, 1.5 mmol) was then added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (10 mL), washed with water (2×4 mL), brine (2×4 mL); dried over anhydrous sodium sulfate and concentrated to give the title compound as a white powder (174 mg, 74%). 1H NMR (300 MHz, CDCl3): δ 6.42 (br, 1H), 3.31 (s, 2H), 1.86 (m, 2H), 1.76 (m, 2H), 1.65 (m, 2H), 1.47 (m, 4H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. washwashed with water (2×4 mL), brine (2×4 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04052d222c8f43dfb60281a128587251
Source dataset
uspto-grants-2009_02
Patent number
US07485722B2

Reaction notes

Loading…