Lithium amide → HCID 86745034, compound

HRID 728095Notes

Reaction equation

HRID 728095 reaction equation
[C:1]([O:11]C)(=O)/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[C:6]([O:8][CH3:9])=[O:7].[CH:13]1([O:19][N:20]2[C:25]([CH3:27])([CH3:26])[CH2:24][CH:23]([OH:28])[CH2:22][C:21]2([CH3:30])[CH3:29])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[NH2-:31].[Li+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:6]([O:8][CH:9]1[CH2:27][C:25]([CH3:24])([CH3:26])[N:31]([O:19][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:21]([CH3:30])([CH3:29])[CH2:22]1)(=[O:7])/[CH:5]=[CH:4]/[CH:3]=[CH:2]/[C:1]([O:28][CH:23]1[CH2:22][C:21]([CH3:30])([CH3:29])[N:20]([O:19][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:25]([CH3:26])([CH3:27])[CH2:24]1)=[O:11]

Participants

6

Reactant 3

HCID 24532Lithium amideHCID 5370244Dimethyl muconate, (E,E)-HCID 113228111-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

Product 1

HCID 86745034HCID 86745034, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.70 gram of dimethyl trans-transmuconate, 5.62 grams of 1-cyclohexyloxy-2,2,6,6-tetra-methylpiperidin-4-ol and 0.025 gram of lithium amide in 100 ml of toluene is heated under reflux with a Dean-Stark trap for 8 hours. The reaction mixture is then diluted with ethyl acetate, and then washed with water, brine and dried over anhydrous magnesium sulfate. Concentration under reduced pressure followed by chromatographic separation affords the title compound as a white solid.

Workup

  1. temperatureunder reflux with a Dean-Stark trap for 8 hours
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customfollowed by chromatographic separation

Sources & evidence

ORD record
ord-641ede2d7c894e698772329d4a59ce98
Source dataset
uspto-grants-1991_09
Patent number
US05047489

Reaction notes

Loading…