Acetyl chloride → HCID 58313107, compound

HRID 535151Notes

Reaction equation

HRID 535151 reaction equation
[NH:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][CH:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].CCN(C(C)C)C(C)C.[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[C:25]([N:1]1[C:5]2([CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[CH2:4][CH2:3][CH:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 58313084Ethyl 8-oxa-1-azaspiro[4.5]decane-2-carboxylate

Product 1

HCID 58313107HCID 58313107, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 8-oxa-1-azaspiro[4.5]decane-2-carboxylate (166) (135 mg, 0.63 mmol) in anhydrous dichloromethane (2 mL) was added Hunig's base (0.22 mL, 1.3 mmol) followed by acetyl chloride (0.05 mL, 0.76 mmol) and the reaction stirred at room temperature under nitrogen for 1.5 h. The reaction was diluted with dichloromethane and washed with 0.1 N HCl and the organic layer dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 60-100% hexanes/EtOAc to afford the title compound as a yellow oil (94 mg, 58% yield).

Workup

  1. washwashed with 0.1 N HCl
  2. dry with materialthe organic layer dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 60-100% hexanes/EtOAc

Sources & evidence

ORD record
ord-ca55592df88b4d478bc6adfb70780bda
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

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