Dimethylformamide → HCID 67264893, compound

HRID 1685147Notes

Reaction equation

HRID 1685147 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:30][CH2:31]OS(C)(=O)=O)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:37]1[CH2:43][CH2:42][CH2:41][C@@H:38]1[CH2:39][OH:40].CN(C=O)C>CC(=O)OCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:15]([CH2:30][CH2:31][N:37]3[CH2:43][CH2:42][CH2:41][C@@H:38]3[CH2:39][OH:40])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:28])([F:29])[F:27])[CH:20]=3)[N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2724541Prolinol, (R)-HCID 86641599HCID 86641599, compound

Product 1

HCID 67264893HCID 67264893, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add 4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-methanesulfonyloxy-ethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (500 mg; 1 equiv; 933 μmol); D-prolinol (3.00 equiv; 2.80 mmol; 283 mg); DMF (1 mL) and heat at 50° C. for 18 h in a sealed vessel. Dilute with EA, wash with saturated sodium bicarbonate, brine, dry MgSO4, filter and purify on 40 g silica gel with 1-10% MeOH/DCM to provide the title compound (506.9 mg; 0.94 mmol; 100%). MS (ES+): m/z=541 (M+H).

Workup

  1. washwash with saturated sodium bicarbonate, brine, dry MgSO4
  2. filtrationfilter
  3. custompurify on 40 g silica gel with 1-10% MeOH/DCM

Sources & evidence

ORD record
ord-3a8b90b22a814e248f1f50c978213594
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

Loading…