Piperidine → HCID 69175643, compound

HRID 2237728Notes

Reaction equation

HRID 2237728 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][C@H:8]([CH:22]([CH3:24])[CH3:23])[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@@H:11]2[CH2:13][O:12]2)=[CH:5][C:4]=1[O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32].[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C(O)(C)C>[OH:12][C@H:11]([C@@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][C@H:8]([CH2:7][C:6]1[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[C:4]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:5]=1)[CH:22]([CH3:24])[CH3:23])[CH2:13][N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 59849018HCID 59849018, compound

Product 1

HCID 69175643HCID 69175643, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 0.25 g of tert-butyl {3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methyl-1(S)-(R)-oxiranylpentyl}carbamate in 4 ml of isopropanol and 0.99 ml of piperidine is stirred at 70° C. over 1 hour. The reaction mixture is concentrated by evaporation, and the residue is admixed with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a colourless oil. Rf=0.24 (9:1 dichloromethane-methanol); Rt=17.40 (gradient II).

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted with tert-butyl methyl ether (2×)
  3. washThe combined organic phases are washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fa1eda9064144cb2bddb989d7000d9e5
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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