Methyl chloroformate → HCID 178501928, compound

HRID 921960Notes

Reaction equation

HRID 921960 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6](/[CH:7]=[N:8]/[C@@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[OH:15])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:27](Cl)(=[O:30])[O:28][CH3:29]>CO>[OH:15][C@H:10]1[C@H:9](/[N:8]=[CH:7]/[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=2)[CH2:14][CH2:13][N:12]([C:27]([O:28][CH3:29])=[O:30])[CH2:11]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 178491124HCID 178491124, compound

Product 1

HCID 178501928HCID 178501928, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3R,4R)-4-((E)-(4-methoxybenzylidene)amino)piperidin-3-ol (400 mg, 1.707 mmol) and DIPEA (0.447 mL, 2.56 mmol) in MeOH (50 mL) at 0° C. (ice bath) was treated with Methyl Chlorocarbonate (1 mL, 12.94 mmol). The reaction was stirred for 12 hour, and then the mixture was concentrated. The crude material was diluted with MeOH and applied on a SCX column (Phenomenex, Strata XC). The column was eluted with 2N ammonia in methanol and solvent removed to afford (3R,4R)-methyl 3-hydroxy-4-((E)-(4-methoxybenzylidene)amino)piperidine-1-carboxylate (499 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe crude material was diluted with MeOH
  3. washThe column was eluted with 2N ammonia in methanol and solvent
  4. customremoved

Sources & evidence

ORD record
ord-82b69609e19f4c55b663b2b50ebb5289
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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