1,1-Dichloroethane → HCID 22038034, compound

HRID 1790430Notes

Reaction equation

HRID 1790430 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].ClC(Cl)C>C(O)(=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=3)[CH2:6][CH2:7]2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 130983796-Bromo-2,3-dihydro-1H-indole

Product 1

HCID 22038034HCID 22038034, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Triacetoxylated sodium borohydride (11.7 g) was added to a mixture of 6- bromoindoline (8.3 g), 1-(t-butoxycarbonyl)-4-piperidone (10 g, [CAS Registry No. 7909-07-3]), acetic acid (14.9 g) and dichloroethane (200 ml) followed by stirring overnight. Then the reaction solution was concentrated under reduced pressure, and the pH value thereof was adjusted to 9 with ethyl acetate, an 8 N aqueous solution of sodium hydroxide and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (10.3 g) (yield: 64%).

Workup

  1. concentrationThen the reaction solution was concentrated under reduced pressure
  2. customan 8 N aqueous solution of sodium hydroxide and water and the layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-2a3e382943c5490cadfd94645bfca5a0
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

Loading…