Decanoyl chloride → HCID 22167009, compound

HRID 1031932Notes

Reaction equation

HRID 1031932 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][C:4]2([CH2:11][C:10](=[O:12])[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][Br:17])[C:8](=[O:18])[CH2:7]2)[CH2:3]1.[C:19](Cl)(=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CC#N>[C:19]([O:1][CH:2]1[CH2:6][CH2:5][C:4]2([CH2:7][C:8](=[O:18])[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][Br:17])[C:10](=[O:12])[CH2:11]2)[CH2:3]1)(=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 66982Decanoyl chlorideHCID 15169808HCID 15169808, compound

Product 1

HCID 22167009HCID 22167009, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

2-Hydroxy-8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9dione (2.55 g, 1.00 equiv) was dissolved in 100 mL of anhydrous CH3CN and cooled in an ice-water bath to 0° C. Decanoyl chloride (1.80 mL, 1.08 equiv) was added dropwise neat. The ice-water bath was removed and the reaction was stirred an additional 18 h. The solvent was removed in vacuo and the resultant oil was flash chromatographed with 20% EtOAc/hexane to yield the title compound (3.03 g, 80%) as a clear liquid.

Workup

  1. customThe ice-water bath was removed
  2. customThe solvent was removed in vacuo
  3. customchromatographed with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-1c8006c8bc074d99a51a84bea14e4168
Source dataset
uspto-grants-1990_09
Patent number
US04956368

Reaction notes

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