Water → Tert-butyl 4-(hydroxymethyl)-4-(methoxymethyl)piperidine-1-carboxylate

HRID 1910404Notes

Reaction equation

HRID 1910404 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([C:17](OCC)=[O:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[H-].C([Al+]CC(C)C)C(C)C.O>C1(C)C=CC=CC=1>[OH:18][CH2:17][C:4]1([CH2:3][O:2][CH3:1])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 667414481-Tert-butyl 4-ethyl 4-(methoxymethyl)piperidine-1,4-dicarboxylate

Product 1

HCID 68533155Tert-butyl 4-(hydroxymethyl)-4-(methoxymethyl)piperidine-1-carboxylateYield 53.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1-tert-butyl 4-ethyl 4-(methoxymethyl)piperidine-1,4-dicarboxylate (2.05 g) in toluene (21 ml) was added 0.99 M solution of diisobutyl aluminum hydride in toluene (16.5 ml) under at 0° C. It was stirred at room temperature for 2 hours. Water was added and extracted with EtOAc. The organic phase was washed with water and brine, dried over MgSO4, evaporated off. The residue was purified by silica gel column to give tert-butyl 4-(hydroxymethyl)-4-(methoxymethyl)piperidine-1-carboxylate (0.95 g) as oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated off
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-2797af7e864445298a079f5b512c8fbf
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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