HCID 15169808, compound → HCID 15068019, compound

HRID 1031931Notes

Reaction equation

HRID 1031931 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.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[O:1]=[C: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

Participants

4

Reactant 2

HCID 15169808HCID 15169808, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15068019HCID 15068019, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Hydroxy-8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9dione-(15.92 g, 1.00 equiv) was dissolved in 100 mL of CH2Cl2 and added to a solution of PCC (120 g, 11 equiv) in 500 mL of CH2Cl2 and stirred at room temperature for 2 h. The solution was filtered through a bed of celite and the salts were washed with CH2Cl2. The solvent was evaporated in vacuo to give a red-brown sludge which was flash chromatographed in 20% EtOAc/hexane to afford the title compound (15.50 g, 98%) as a clear oil.

Workup

  1. filtrationThe solution was filtered through a bed of celite
  2. washthe salts were washed with CH2Cl2
  3. customThe solvent was evaporated in vacuo
  4. customto give a red-brown sludge which
  5. customchromatographed in 20% EtOAc/hexane

Sources & evidence

ORD record
ord-43f05be5abef445fb622760a9310a04c
Source dataset
uspto-grants-1990_09
Patent number
US04956368

Reaction notes

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