Potassium sodium tartarate → (1-Isopropylpiperidin-4-yl)methanol

HRID 1883070Notes

Reaction equation

HRID 1883070 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](OCC)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 19900430Ethyl 1-isopropylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11147855(1-Isopropylpiperidin-4-yl)methanolYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 1-isopropylpiperidine-4-carboxylate (10.0 g, 50.2 mmol) in THF (250 mL) at 0° C. was treated with lithium aluminum hydride (2.1 g, 55 mmol). After 1 h, the mixture was treated with a saturated aqueous solution of sodium potassium tartrate, partitioned with EtOAc, and the aqueous layer washed with EtOAc (2×). The combined extracts were dried (Na2SO4), concentrated, and the residue purified by column chromatography (SiO2: 10% methanol:methylene chloride) affording 4.30 g (54%) of the title compound.

Workup

  1. custompartitioned with EtOAc
  2. washthe aqueous layer washed with EtOAc (2×)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue purified by column chromatography (SiO2: 10% methanol:methylene chloride)

Sources & evidence

ORD record
ord-9d9e5e6527f34dc9bae7d55f23d41f85
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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