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

1,4-Dibromo-2-butanol → (4aRS,5SR,8aRS)-1-benzyl-5-(3-hydroxypyrrolidin-1-yl)perhydroquinoxaline-2,3-dione

HRID 1876803
Notes
Print preview

Reaction equation

HRID 1876803 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][CH2:9][CH:8]2[CH:3]1[NH:4][C:5](=[O:20])[C:6](=[O:19])[N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+].Br[CH2:27][CH:28]([OH:32])[CH2:29][CH2:30]Br>C(#N)C>[CH2:12]([N:7]1[CH:8]2[CH:3]([CH:2]([N:1]3[CH2:30][CH2:29][CH:28]([OH:32])[CH2:27]3)[CH2:11][CH2:10][CH2:9]2)[NH:4][C:5](=[O:20])[C:6]1=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 295701,4-Dibromo-2-butanolHCID 516892Sodium BicarbonateHCID 68777664(4aRS,5SR,8aRS)-5-amino-1-benzylperhydroquinoxaline-2,3-dione

Product 1

HCID 68778432(4aRS,5SR,8aRS)-1-benzyl-5-(3-hydroxypyrrolidin-1-yl)perhydroquinoxaline-2,3-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4aRS,5SR,8aRS)-5-Amino-1-benzylperhydroquinoxaline-2,3-dione (144 mg, 0.53 mmol) was dissolved in acetonitrile (16 ml), and NaHCO3 (300 mg, 3.57 mmol) and racemic 1,4-dibromobutan-2-ol (purity 85%, 1.15 g, 4.20 mmol, 0.57 ml) were added. After 24 hours, NaHCO3 was separated off and the mixture was evaporated in vacuo. The solid was taken up in CH2Cl2 and the mixture was extracted by shaking three times with HCl (1 N). The aqueous phase was then brought to pH 8 with NaOH (2 N) and extracted by shaking three times with CH2Cl2. The organic phases were dried over Na2SO4 and evaporated in vacuo. The crude product was purified by flash chromatography over silica gel 60 (40-63 μm, (Merck) Ø 2 cm, acetone/MeOH/Et2NH 9.5:0.5:0.1, l=17 cm, V=5 ml). A pale yellow solid was isolated.

Workup

  1. customNaHCO3 was separated off
  2. customthe mixture was evaporated in vacuo
  3. extractionthe mixture was extracted
  4. extractionextracted
  5. stirringby shaking three times with CH2Cl2
  6. dry with materialThe organic phases were dried over Na2SO4
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography over silica gel 60 (40-63 μm, (Merck) Ø 2 cm, acetone/MeOH/Et2NH 9.5:0.5:0.1, l=17 cm, V=5 ml)
  9. customA pale yellow solid was isolated

Sources & evidence

ORD record
ord-7d8d99e8c42741f1b0735069a8d4fb7c
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309725B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes