tert-Butyl (3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-ylcarbamate → (3SR,5SR)-1-Amino-3-(2-chloro-4-fluorophenyl)-5-hydroxypiperidin-2-one

HRID 451521Notes

Reaction equation

HRID 451521 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH:13]([OH:15])[CH2:12][N:11]([NH:16]C(=O)OC(C)(C)C)[C:10]1=[O:24]>Cl>[NH2:16][N:11]1[CH2:12][CH:13]([OH:15])[CH2:14][CH:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Cl:1])[C:10]1=[O:24]

Participants

3

Reactant 1

HCID 86656716tert-Butyl (3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-ylcarbamate

Product 1

HCID 67344225(3SR,5SR)-1-Amino-3-(2-chloro-4-fluorophenyl)-5-hydroxypiperidin-2-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To tert-butyl (3SR,5SR)-3-(2-chloro-4-fluorophenyl)-5-hydroxy-2-oxopiperidin-1-ylcarbamate (1.67 g, 4.7 mmol) was added HCl (10 mL, 4 N in dioxane) and the reaction stirred for 1 hour. The reaction was then concentrated to dryness, redissolved in dichloromethane, washed with sodium hydrogen carbonate, dried with sodium sulfate and the solvent was evaporated in vacuo afford the title compound was obtained as a light yellow crystalline solid (1.11 g, 92%). MS ISP (m/e): 259.1 [(M+H)+].

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. dissolutionredissolved in dichloromethane
  3. washwashed with sodium hydrogen carbonate
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e8ed8d671e6e418ca91eee299954afc6
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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