1,1'-Carbonyldiimidazole → HCID 19029344, compound

HRID 2294993Notes

Reaction equation

HRID 2294993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][C:15]([N:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH3:18])=[O:16])[CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+]>CCOC(C)=O.CN(C1C=CN=CC=1)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][CH2:11][OH:12])[CH2:14][C:15]([N:17]([CH3:18])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 21472505HCID 21472505, compound

Product 1

HCID 19029344HCID 19029344, compoundYield 96.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Treat the acid from Step 4 (9.3 g) in EtOAc (100 mL) with 1,1'-carbonyldiimidazole (4.62 g) and DMAP (345 mg), stir the resulting solution at room temperature for 15 min., then heat at 50° C. for 1 h. Cool the reaction mixture to 0° C. and treat with a solution of NaBH4 (3.45 g) in H2O (50 mL), warm slowly to room temperature and stir for 12 h. Dilute the reaction mixture with EtOAc (250 mL) and wash with 1N HCl (1×100 mL) and H2O (1×100 mL), dry over MgSO4, filter and concentrate under reduced pressure to yield a crude oil (13 g). Chromatograph on silica gel, eluting with 5% CH3 OH/CH2Cl2 to give 3,4-dichloro-β-(2-hydroxyethyl)-N-methyl-N-[(2-methoxyphenyl) methyl]benzenepropanamide (8.7 g). HRMS (FAB, M+H+): m/e cal'd for [C20H24NO3Cl2 ]+ 396.1133; found 396.1124.

Workup

  1. temperatureheat at 50° C. for 1 h
  2. temperatureCool the reaction mixture to 0° C.
  3. temperaturewarm slowly to room temperature
  4. stirringstir for 12 h
  5. washwash with 1N HCl (1×100 mL) and H2O (1×100 mL)
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customto yield a crude oil (13 g)
  10. washChromatograph on silica gel, eluting with 5% CH3 OH/CH2Cl2

Sources & evidence

ORD record
ord-8b5c0943ba784dfa96eb5c812cf19fb2
Source dataset
uspto-grants-1997_11
Patent number
US05691362

Reaction notes

Loading…