HCID 69856072, compound → HCID 22639973, compound

HRID 2415115Notes

Reaction equation

HRID 2415115 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:6][N:7]1[C:12](=O)[CH2:11][CH:10]([OH:14])[CH2:9][CH:8]1[CH2:15][CH2:16][CH:17]1[CH:26]2[C:21](=[CH:22][CH:23]([CH3:34])[CH2:24][CH:25]2[O:27]C(=O)C(C)CC)[CH:20]=[CH:19][CH:18]1[CH3:35]>C1COCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([OH:14])[CH2:9][CH:8]1[CH2:15][CH2:16][CH:17]1[CH:26]2[C:21](=[CH:22][CH:23]([CH3:34])[CH2:24][CH:25]2[OH:27])[CH:20]=[CH:19][CH:18]1[CH3:35]

Participants

4

Reactant 1

HCID 69856072HCID 69856072, compound

Product 1

HCID 22639973HCID 22639973, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 600 mg (1.1 mmol) of 2-methyl-butyric acid 8-(2-[1-(3,4-dimethyoxy-benzyl)-4-hydroxy-6-oxopiperidin-2-yl]-ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester in 15 ml of THF at rt are added 2 ml of a 65% RedAl® solution in toluene. After 3 hours, the reaction is quenched by the addition of 1 ml of methanol. The organic phase is extracted twice with 15 ml of 2N HCl. The aqueous phases are combined, brought to pH 12 with 1N NaOH and extracted three times with ethyl acetate. The organic phases are combined, dried over sodium sulfate and the solvent evaporated. The residue is purified by silica gel chromatography (t-butyl methyl ether/methanol 9/1) to afford pure 1-(3,4-Dimethoxy-benzyl)-2-[2-(8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-piperidin-4-ol as a white foam.

Workup

  1. customthe reaction is quenched by the addition of 1 ml of methanol
  2. extractionThe organic phase is extracted twice with 15 ml of 2N HCl
  3. extractionextracted three times with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated
  6. customThe residue is purified by silica gel chromatography (t-butyl methyl ether/methanol 9/1)

Sources & evidence

ORD record
ord-f60075df249d45f893eb8cfcf5e1ab95
Source dataset
uspto-grants-2004_11
Patent number
US06818638B2

Reaction notes

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