HCID 178418365, compound → HCID 178451763, compound

HRID 1044339Notes

Reaction equation

HRID 1044339 reaction equation
C([Mg]Br)(C)C.[OH:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][CH2:14][CH2:15][C:16]2([C:29](OCC)=[O:30])[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH2:9][CH2:8]1>O>[OH:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:14][CH2:15][C:16]3([CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:17]3)[C:29]2=[O:30])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 178418365HCID 178418365, compoundHCID 178469230HCID 178469230, compound

Product 1

HCID 178451763HCID 178451763, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

iso-Propylmagnesium bromide (1.0 M in THF, 1.5 mL) was slowly added to a solution of 1-tert-butyl 3-ethyl 3-{2-[(cis-4-hydroxycyclohexyl)amino]ethyl}piperidine-1,3-dicarboxylate (0.15 g, 0.38 mmol) at 0° C. and the mixture was stirred at this temperature for 1 h. The reaction was then poured into cold water and extracted with ethyl acetate, dried and concentrated to give the desired product (0.11 g, 85%). LC-MS: 353.2 (M+H)+, 297.1 (M+H-56)+.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-381b36867aaf400bbf79bad9ebbc2cdc
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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