Water → HCID 53948261, compound

HRID 1060184Notes

Reaction equation

HRID 1060184 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]2[N:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][C:12](=[O:21])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]2[CH2:11][C:12](=[O:21])[CH2:13][CH2:14][N:15]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 962WaterHCID 3611392Lithium tri-s-butylborohydrideHCID 57105160HCID 57105160, compound

Product 1

HCID 53948261HCID 53948261, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Intermediate 9 (0.176 mol) in THF (880 ml) was stirred under a N2 flow, and cooled to −78° C. L-selectride (0.264 mol) was added dropwise at −78° C. The reaction mixture was stirred for 1 hour, then poured out into water. DIPE was added. The organic layer was separated, washed with an aqueous NaHCO3 solution, with an aqueous NaCl solution, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10). The desired fractions were collected and the solvent was evaporated, yielding 20.2 g (34.8%) of (±)-ethyl 2-[(3,4-dichlorophenyl)methyl]-4-oxo-1-piperidinecarboxylate (intermediate 10).

Workup

  1. additionDIPE was added
  2. customThe organic layer was separated
  3. washwashed with an aqueous NaHCO3 solution, with an aqueous NaCl solution
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10)
  8. customThe desired fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0e7ef66947844c519b74159cd041cb09
Source dataset
uspto-grants-2003_02
Patent number
US06521621B1

Reaction notes

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