HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethylene Glycol → tert-butyl (3R)-4-[3-(2-hydroxyethoxy)pyrazin-2-yl]-3-methylpiperazine-1-carboxylate

HRID 1295727
Notes
Print preview

Reaction equation

HRID 1295727 reaction equation
Cl[C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@H:9]2[CH3:21])=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:22]([OH:25])[CH2:23][OH:24].CC([O-])(C)C.[K+]>CS(C)=O>[OH:24][CH2:23][CH2:22][O:25][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@H:9]2[CH3:21])=[N:4][CH:5]=[CH:6][N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 23665647Potassium tert-butoxideHCID 86591091(R)-tert-butyl 4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 69366745tert-butyl (3R)-4-[3-(2-hydroxyethoxy)pyrazin-2-yl]-3-methylpiperazine-1-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl (3R)-4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate* (35 g, 0.11 mol), ethylene glycol (100 g, 1.61 mol) and t-BuOK (25 g, 0.22 mol) in DMSO (150 g) was stirred at 50° C. for 3 h. After this time, the reaction mixture was partitioned between EtOAc (500 g) and water (500 g) and sodium chloride (20 g) was added. The organic layer was concentrated in vacuo to furnish 32.5 g (87%) of the title product. HPLC purity: 75%. HRMS m/z calcd for C16H26N4O4 (M)+ 338.1954, found 338.1959. *Described in WO 00/76984, Example 172, Step 2.

Workup

  1. customAfter this time, the reaction mixture was partitioned between EtOAc (500 g) and water (500 g) and sodium chloride (20 g)
  2. additionwas added
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-0e0738a5d6b84072a849fcf60a9332a9
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07244722B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes