HCID 57147682, compound → HCID 57110190, compound

HRID 1459404Notes

Reaction equation

HRID 1459404 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].[CH3:33][Mg]Br>C(OCC)C>[C:8]12([NH:7][C:5](=[O:6])[C:4]([CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)([CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:3](=[O:2])[CH3:33])[CH2:15][CH:14]3[CH2:16][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:17]1)[CH2:9]2

Participants

4

Reactant 2

HCID 57147682HCID 57147682, compoundHCID 178418573HCID 178418573, compound3×

Product 1

HCID 57110190HCID 57110190, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of N-adamantan-1-yl-2,2-bis-pyridin4-ylmethyl-malonamic acid methyl ester (750 mg, 1.68 mmol) chilled to 5 ° C., cuprous bromide (10.0 mg) and a 3.0M solution of methyl magnesium bromide in diethyl ether (1.67 ml, 5.03 mmol of methyl magnesium bromide) was added. After 18 hours stirring at ambient temperature, a second 1.67 ml portion of 3.0M methyl magnesium bromide in diethyl ether was added. Three hours thereafter, a final 1.67 ml portion of 3.0M methyl magnesium bromide was added. After 18 hours of additional stirring at ambient temperature, the reaction was quenched by addition of 15 ml of ice water containing 250 μl of concentrated sulfuric acid. The mixture was then extracted with three 50 ml portions of methylene chloride. The combined extracts were dried (anhydrous sodium sulfate) and concentrated in vacuo to an oil (520 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 (free base) as a colorless oil (236 mg).

Workup

  1. stirringAfter 18 hours of additional stirring at ambient temperature
  2. customthe reaction was quenched by addition of 15 ml of ice water containing 250 μl of concentrated sulfuric acid
  3. extractionThe mixture was then extracted with three 50 ml portions of methylene chloride
  4. dry with materialThe combined extracts were dried (anhydrous sodium sulfate)
  5. concentrationconcentrated in vacuo to an oil (520 mg)
  6. 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-c4818b51165a4e4492f9a4aef8b04dde
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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