Triethylamine → HCID 3828237, compound

HRID 2363998Notes

Reaction equation

HRID 2363998 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.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C(OCC)(=O)C>[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:19]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 3828237HCID 3828237, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1,4-dioxa-8-azaspiro[4.5]decane (2.00 g, 13.9 mmol) and triethylamine (2.90 mL, 20.9 mmol) in ethyl acetate (50 mL) at 0° C. was added phenyl chloroformate (2.10 mL, 13.9 mmol). The mixture was allowed to warm to room temperature overnight. Then, the mixture was filtered to remove triethylamine hydrochloride salts. The filtrate was concentrated, and the obtained residue was chromatographed (silica gel, hexanes to 50:50 hexanes/ethyl acetate) to give the title compound (3.48 g, 95%) as a white solid:

Workup

  1. filtrationThen, the mixture was filtered
  2. customto remove triethylamine hydrochloride salts
  3. concentrationThe filtrate was concentrated
  4. customthe obtained residue was chromatographed (silica gel, hexanes to 50:50 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-271cecbefb5a4605ab851763c0f9ba20
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

Loading…