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

1,2-Dimethoxyethane → HCID 59769440, compound

HRID 32174
Notes
Print preview

Reaction equation

HRID 32174 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][C:15]=2OS(C(F)(F)F)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCOC.CC1(C)C(C)(C)OB([C:48]2[CH2:55][CH2:54][C:51]3([CH2:53][CH2:52]3)[CH2:50][CH:49]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[CH:16][C:15]=2[C:48]2[CH2:55][CH2:54][C:51]3([CH2:53][CH2:52]3)[CH2:50][CH:49]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 231425414,4,5,5-Tetramethyl-2-(spiro[2.5]oct-5-en-6-yl)-1,3,2-dioxaborolaneHCID 86601817HCID 86601817, compound

Product 1

HCID 59769440HCID 59769440, compoundYield 90.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent2×
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-(4-morpholin-4-yl-2-trifluoromethanesulfonyloxyphenyl)piperazine-1-carboxylic acid t-butyl ester (1.49 g, 3.01 mmol), 1,2-dimethoxyethane (15 mL), water (1 mL), 4,4,5,5-tetramethyl-2-spiro[2.5]oct-5-en-6-yl-[1,3,2]dioxaborolane (1.13 g, 4.82 mmol) produced in Example (34b), tetrakis(triphenylphosphine)palladium(0) (278 mg, 0.241 mmol) and tripotassium phosphate (1.23 g, 5.78 mmol) was stirred for 13 hours and 20 minutes at an external temperature of 80-90° C. under a nitrogen atmosphere. Ethyl acetate and brine were added to the reaction mixture and extraction was performed three times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the desiccant was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 1.23 g of the title compound as a colorless solid.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. filtrationthe desiccant was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cb88890f51904a0d8868de6447953571
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425554B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes