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

HRID 430618Notes

Reaction equation

HRID 430618 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, was 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 a mixture of ethyl ether and petroleum ether 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 a mixture of ethyl ether and petroleum ether

Sources & evidence

ORD record
ord-6466b58dd67b434d9a80846a2319868d
Source dataset
uspto-grants-2001_11
Patent number
US06323214B1

Reaction notes

Loading…