Water → HCID 89923005, compound

HRID 921961Notes

Reaction equation

HRID 921961 reaction equation
[OH:1][C@H:2]1[C@H:7](/[N:8]=C/C2C=CC(OC)=CC=2)[CH2:6][CH2:5][N:4]([C:18]([O:20][CH3:21])=[O:19])[CH2:3]1.O.C(O)(C(F)(F)F)=O>CO>[NH2:8][C@@H:7]1[CH2:6][CH2:5][N:4]([C:18]([O:20][CH3:21])=[O:19])[CH2:3][C@H:2]1[OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 178501928HCID 178501928, compound

Product 1

HCID 89923005HCID 89923005, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (3R,4R)-methyl 3-hydroxy-4-((E)-(4-methoxybenzylidene)amino)piperidine-1-carboxylate (499 mg, 1.707 mmol) in MeOH (17 ml) was added water (1 ml, 55.5 mmol) and TFA (2 ml, 26.0 mmol). The reaction was stirred at 50° C. overnight. The reaction mixture was applied on a SCX column (Phenomenex, Strata XC) and eluted with 2N ammonia in methanol. The solvents removed to afford (3R,4R)-methyl 4-amino-3-hydroxypiperidine-1-carboxylate (290 mg).

Workup

  1. washeluted with 2N ammonia in methanol
  2. customThe solvents removed

Sources & evidence

ORD record
ord-e1886f81ed344efa84d841d3fa55e721
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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