Aluminium lithium hydride → HCID 18457678, compound

HRID 853766Notes

Reaction equation

HRID 853766 reaction equation
[C:1]1([CH:7]2[NH:12][CH:11]([C:13](OC)=[O:14])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[C:1]1([CH:7]2[NH:12][CH:11]([CH2:13][OH:14])[CH2:10][CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69472200HCID 69472200, compound

Product 1

HCID 18457678HCID 18457678, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 6-phenylpipecolinate (0.23 g) in THF (15 mL) was treated with 1M lithium aluminum hydride in ether (10 mL) at room temperature for 2 h. The reaction mixture was quenched with EtOAc, then MgSO4 was added and the mixture was filtered. The filtrate was concentrated to give a residue, which was purified by chromatography on silica gel plates (2, 1000 μm) using EtOAc:hexane 1:1 as the eluent, to give (6-phenyl-piperidin-2-yl)-methanol as a white solid (0.06 g).

Workup

  1. customThe reaction mixture was quenched with EtOAc
  2. additionMgSO4 was added
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated
  5. customto give a residue, which
  6. customwas purified by chromatography on silica gel plates (2, 1000 μm)

Sources & evidence

ORD record
ord-07abb69e723947b594898b3582cb6184
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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