Ethyl Acetate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1848429Notes

Reaction equation

HRID 1848429 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11][CH:10]([C:13](OC)=[O:14])[CH2:9][CH2:8]1.C(OCC)(=O)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[OH:14][CH2:13][CH:10]1[CH2:11][CH2:12][N:7]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 70 g of LiAlH4 in 1500 mL of THF was cooled to 0° C., then 180 g of 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate in THF was added dropwise. When the reaction was finished, 200 mL of ethyl acetate and solid anhydrous Na2SO4. Water was added until the solution became clear. The mixture was filtered and the filtrate was evaporated to afford the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-ee3d6c3bb13548f68e9260a95215b193
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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