Triethylamine → Phenylmethyl 1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate

HRID 566948Notes

Reaction equation

HRID 566948 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:18]([O:25][C:26](Cl)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[CH2:18]([O:25][C:26]([N:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 15165038Phenylmethyl 1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well-stirred and ice-cooled solution of 1,4-dioxa-8-azaspiro[4,5]decane (34.9 mmol, 5 g) in dichloromethane (200 mL) under an argon atmosphere, is added triethylamine (52.4 mmol, 7.3 mL) and then benzyloxycarbonyl chloride (42 mmol, 5.93 mL) dropwise. The suspension was stirred at room temperature for 24 hours and the precipitated solid was filtered. The organic solution was evaporated under vacuum to give an oily residue which was chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture to afford 8-benzyloxycarbonyl 1,4-dioxa-8-azaspiro [4,5] decane in quantitative yield. 1H-NMR (CDCl3): 1.63 (m, 4H); 3.56 (m,4H); 3.89 (s, 4H); 5.09 (s, 2H); 7.28 (s, 5H).

Workup

  1. stirringThe suspension was stirred at room temperature for 24 hours
  2. filtrationthe precipitated solid was filtered
  3. customThe organic solution was evaporated under vacuum
  4. customto give an oily residue which
  5. customwas chromatographed on silica gel eluting with ethyl ether and petroleum ether mixture

Sources & evidence

ORD record
ord-23d0d9452f6b4b6fad3c9ef05fefc40d
Source dataset
uspto-grants-2001_01
Patent number
US06177444B1

Reaction notes

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