Triphenylphosphine → HCID 69507028, compound

HRID 540918Notes

Reaction equation

HRID 540918 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([OH:17])=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:18]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:42]1[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH:42]4[CH2:47][CH2:46][N:45]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:44][CH2:43]4)=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:18]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 136347854HCID 136347854, compound

Product 1

HCID 69507028HCID 69507028, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-ol (3.00 g, 10.5 mmol) and triphenylphosphine (3.43 g, 13.1 mmol) were slurried in THF (105 mL) and cooled with an ice/water bath. tert-Butyl 4-hydroxypiperidine-1-carboxylate (2.64 g, 13.1 mmol) was added followed by the dropwise addition of diisopropyl azodicarboxylate (2.58 mL, 13.1 mmol). The water bath was removed and the mixture was stirred for 72 hours under nitrogen. The solvent was removed under reduced pressure and the residue was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 1-15% CMA in chloroform) to afford 5.17 g of tert-butyl 4-{[2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}piperidine-1-carboxylate as an off-white crystalline solid.

Workup

  1. temperaturecooled with an ice/water bath
  2. customThe water bath was removed
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 1-15% CMA in chloroform)

Sources & evidence

ORD record
ord-edbcf0271a824362a8e2c009a07f5e50
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

Loading…