tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 178498449, compound

HRID 1458418Notes

Reaction equation

HRID 1458418 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([NH2:17])=[CH:9][C:7]=2[N:8]=1)([CH3:3])[CH3:2].[C:18]([O:22][C:23](N1CCC(=O)CC1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CO.[C:34](O)(=O)[CH3:35]>>[CH:1]([C:4]1[NH:5][C:6]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([N:17]([CH:35]3[CH2:34][CH2:6][NH:5][CH2:4][CH2:1]3)[C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])=[CH:9][C:7]=2[N:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 10129899Acetic acid methanolHCID 178498398HCID 178498398, compound

Product 1

HCID 178498449HCID 178498449, compound

Procedure

To 2-isopropyl-4-methoxycarbonyl-6-aminobenzimidazole in methanol/acetic acid (300 mL, 2:1, v/v) was added N-tert-butoxycarbonyl-4-piperidone (80 g), followed by NaCNBH4 (9 g) at ambient temperature. After stirring at ambient temperature for 1 hour the solvents were removed and the resulting residue was worked up between ethyl acetate and H2O. The organic layer was dried, concentrated, and purified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient) to afford 2-isopropyl-4-methoxycarbonyl-6-(N-(tert-butoxycarbonyl)piperidin-4-ylamino)benzimidazole as a foam.

Workup

  1. customfollowed by NaCNBH4 (9 g) at ambient temperature
  2. customwere removed
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient)

Sources & evidence

ORD record
ord-970755256793480c84c95c12ad64aa93
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

Loading…