Phenoxyacetyl chloride → 4-Hydroxy-3-[(phenoxyacetyl)amino]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester

HRID 1529558Notes

Reaction equation

HRID 1529558 reaction equation
[O:1]([CH2:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH:21]([NH2:26])[CH2:20]1)=[O:18])([CH3:15])[CH3:14].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:15][C:13]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH:21]([NH:26][C:9](=[O:10])[CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:20]1)=[O:18])([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 69703Phenoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 56932104tert-Butyl 3-amino-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 666093234-Hydroxy-3-[(phenoxyacetyl)amino]-1-piperidinecarboxylic acid 1,1-dimethylethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenoxyacetyl chloride (0.15 mL, 1.06 mmol) was added dropwise to a stirred solution of 3-amino-4-hydroxy-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (0.23 g, 1.06 mmol) and TEA (0.18 mL, 1.27 mmol) in DCM (3 mL) at 0° C. The reaction mixture was stirred at room temperature for 15 minutes and a saturated solution of NaHCO3 was added. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 4-hydroxy-3-[(phenoxyacetyl)amino]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (0.36 g, 98% yield) that was used in the next step without further purification. C18H26N2O5 LCMS: Rt 2.03, m/z 351 [M+H]+ (using method, LC-MS Method 6).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1c619990af3f46c48675c2aee51083fa
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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