Hydrochloric Acid → Tert-butyl 3-(hydroxymethyl)-3-methylpiperidine-1-carboxylate

HRID 1611142Notes

Reaction equation

HRID 1611142 reaction equation
[CH3:1][C:2]1([C:15](OCC)=[O:16])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Li+].[BH4-].Cl>C1COCC1>[OH:16][CH2:15][C:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 205853941-tert-Butyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate

Product 1

HCID 22258928Tert-butyl 3-(hydroxymethyl)-3-methylpiperidine-1-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−20° C.) solution of 1-tert-butyl 3-ethyl 3-methyl-1,3-piperidinedicarboxylate (2.3 g, 8.48 mmol) in dry THF was added LiBH4 (2M in THF, 10.6 mmol), and the stirring was continued overnight. The reaction mixture was allowed to warm to room temperature. The reaction mixture was cooled by ice water and acidified (pH 5-6) with aqueous 1N HCl. The mixture was concentrated under reduced pressure, then extracted with ethyl acetate. The organic phase was separated, dried over MgSO4, filtered, and evaporated. The crude product was purified by column chromatography on silica gel (hexane:ethyl acetate, 4:1-3:1) to give tert-butyl 3-(hydroxymethyl)-3-methyl-1-piperidinecarboxylate as a colorless oil form (1.5 g, yield; 78%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica gel (hexane:ethyl acetate, 4:1-3:1)

Sources & evidence

ORD record
ord-7d1451ea067941ee8dcf439c396bddb7
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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