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Tetrahydrofuran toluene → HCID 17912671, compound

HRID 1459406
Notes
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Reaction equation

HRID 1459406 reaction equation
C[O:2][C:3](=O)[C:4]([CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)([CH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[C:5]([NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:6].C[Mg]Br.C1(C)C=CC=CC=1.O1CCCC1>O1CCCC1>[C:8]12([N:7]3[C:5](=[O:6])[C:4]([CH2:25][C:26]4[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=4)([CH2:18][C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[C:3]3=[O:2])[CH2:9][CH:10]3[CH2:16][CH:14]([CH2:13][CH:12]([CH2:11]3)[CH2:17]1)[CH2:15]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 57147682HCID 57147682, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 17912671HCID 17912671, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-adamantan-1-yl-2,2-bis-pyridin4-ylmethyl-malonamic acid methyl ester (100 mg, 0.23 mmol) in anhydrous tetrahydrofuran (1.5 ml), a 1.4M solution of methyl magnesium bromide in toluene/ tetrahydrofuran (Aldrich Chemical Co., 330 μl, 0.46 mmol of methyl magnesium bromide) and cuprous bromide (1.6 mg) was added. The reaction was heated at 50° C. for 6 hours and then quenched by addition to 15 ml of ice water containing 200 μl of concentrated sulfuric acid. The pH of the mixture was then adjusted to 8.0 with aqueous sodium bicarbonate. Two 15 ml methylene chloride extractions were combined, dried (anhydrous sodium sulfate), and concentrated in vacuo to an oil (104 mg). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with methanol/methylene chloride=4:96 in volume) afforded the title compound (20 mg) as an oil.

Workup

  1. customquenched by addition to 15 ml of ice water containing 200 μl of concentrated sulfuric acid
  2. extractionTwo 15 ml methylene chloride extractions
  3. dry with materialdried (anhydrous sodium sulfate)
  4. concentrationconcentrated in vacuo to an oil (104 mg)
  5. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with methanol/methylene chloride=4:96 in volume)

Sources & evidence

ORD record
ord-c339d3cbefd24b22b5817105120c7754
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05854232

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes