Acetic Acid → O1-tert-butyl O3-methyl 4-hydroxy-3-methyl-piperidine-1,3-dicarboxylate

HRID 712199Notes

Reaction equation

HRID 712199 reaction equation
[CH3:1][C:2]1([C:16]([O:18][CH3:19])=[O:17])[C:7](=[O:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.C(O)(=O)C.C([BH3-])#N.[Na+].O>CO>[OH:8][CH:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:3][C:2]1([CH3:1])[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 667585171-tert-Butyl 3-methyl 3-methyl-4-oxopiperidine-1,3-dicarboxylate

Product 1

HCID 66977046O1-tert-butyl O3-methyl 4-hydroxy-3-methyl-piperidine-1,3-dicarboxylateYield 98.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of O1-tert-butyl O3-methyl 3-methyl-4-oxo-piperidine-1,3-dicarboxylate (0.5 g, 1.85 mmol) in MeOH (10 mL) was added acetic acid (0.5 mL) followed by portion wise addition of sodium cyanoborohydride (0.12 g, 1.85 mmol). The mixture was stirred at rt for 4 h. After completion of reaction (by TLC), water (50 mL) was added and extracted with DCM (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the product as a viscous liquid (0.5 g). MS: 274.13 [M+H]+.

Workup

  1. additionwas added
  2. extractionextracted with DCM (3×100 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b48ff9ebf2e45d5b89d7343180b9724
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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