Acetic Acid → HCID 67602990, compound

HRID 362781Notes

Reaction equation

HRID 362781 reaction equation
[CH3:1][O:2][CH:3]1[C:8](=[O:9])[CH2:7][CH2:6][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].C(O)(=O)C>O1CCCC1>[CH3:1][O:2][C@H:3]1[C@@H:8]([OH:9])[CH2:7][CH2:6][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3611392Lithium tri-s-butylborohydrideHCID 15078438HCID 15078438, compound

Product 1

HCID 67602990HCID 67602990, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

a') A solution of 3-methoxy-1-(phenylmethyl)-4-piperidinone (4.4 g) in tetrahydrofuran was cooled to -75° C. Lithium tris-sec-butylborohydride was added dropwise and the reaction mixture was stirred for 2 hours at -70° C. Acetic acid 10% (100 ml) was added dropwise at room temperature. The organic solvent was evaporated. The aqueous residue was alkalized with NH4OH, then extracted twice with diisopropylether. The separated organic layer was washed with water, dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by short column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5 upgrading to 98/2), yielding 1.3 g (29.4%) of cis-3-methoxy-1-(phenylmethyl)-4-piperidinol (intermediate 2).

Workup

  1. customThe organic solvent was evaporated
  2. extractionextracted twice with diisopropylether
  3. washThe separated organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by short column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5 upgrading to 98/2)

Sources & evidence

ORD record
ord-7aa4de2a3c924e9da746ad4a2832e49a
Source dataset
uspto-grants-1999_02
Patent number
US05872131

Reaction notes

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