Potassium Carbonate → (2R,5S)-4-Benzyloxycarbonylmethyl-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1475483Notes

Reaction equation

HRID 1475483 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[C:19]([O:23][C:24]([N:26]1[CH2:31][C@H:30]([CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][C@H:34]2[CH3:39])[NH:29][CH2:28][C@H:27]1[CH3:40])=[O:25])([CH3:22])([CH3:21])[CH3:20]>C(#N)C>[C:19]([O:23][C:24]([N:26]1[CH2:31][C@H:30]([CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][C@H:34]2[CH3:39])[N:29]([CH2:2][C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH2:28][C@H:27]1[CH3:40])=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 70980298(2R,5S)-tert-butyl 2-methyl-5-(((R)-3-methylmorpholino)methyl)piperazine-1-carboxylate

Product 1

HCID 86724031(2R,5S)-4-Benzyloxycarbonylmethyl-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl esterYield 86.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromoacetate (25.2 mL, 126 mmol) and K2CO3 (50 g, 389 mmol) were added to a solution of (2R,5S)-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (30.5 g, 97.4 mmol) in acetonitrile (300 mL) and the reaction was stirred at room temperature for 18 h. The solid was removed by filtration and the solvent was removed in vacuo. The crude material was purified by chromatography using a pad of silica eluting with EtOAc/Petrol (1/9 to 4/6) to give the title compound (39 g). MS: [M+H]+=462.

Workup

  1. customThe solid was removed by filtration
  2. customthe solvent was removed in vacuo
  3. customThe crude material was purified by chromatography

Sources & evidence

ORD record
ord-69e879c5571a42a29780861834cabf02
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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