Triethylamine → HCID 58313162, compound

HRID 1748865Notes

Reaction equation

HRID 1748865 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:4][CH:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:2]1.C(N(CC)CC)C.[CH2:23]([O:30][C:31](Cl)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[CH2:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:4][C@@H:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:2]1[C:31]([O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 58313067HCID 58313067, compound

Product 1

HCID 58313162HCID 58313162, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 8-oxa-2-azaspiro[4.5]decane-3-carboxylate (3.54 g, 16.6 mmol) was dissolved in dry dichloromethane (80 mL), triethylamine (5.8 mL, 41.5 mmol) was added followed by benzylchloroformate (3.5 mL, 24.9 mmol) and the reaction is stirred at room temperature for 2 h under nitrogen. The reaction was diluted with dichloromethane, washed with 0.2 N HCl, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 20-100% hexanes/EtOAc to afford a yellow oil. The racemate was then separated by chiral HPLC on a 10 μm OD column eluting with 25% isopropanol in hexanes to afford the title compound as a clear oil (1.66 g, 29% yield).

Workup

  1. washwashed with 0.2 N HCl
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 20-100% hexanes/EtOAc
  6. customto afford a yellow oil
  7. customThe racemate was then separated by chiral HPLC on a 10 μm OD column
  8. washeluting with 25% isopropanol in hexanes

Sources & evidence

ORD record
ord-5159ac2d8ff34887802108237f8aaedd
Source dataset
uspto-grants-2015_10
Patent number
US09150587B2

Reaction notes

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