Magnesium → N-Boc-2-amino-4-(2,2,5,5-tetramethyl-1-cyclopentyl)-3-butene

HRID 746168Notes

Reaction equation

HRID 746168 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[CH2:9]Br.[Mg].[C:13]([NH:20][C@@H:21]([CH:23]=O)[CH3:22])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CCOCC>[C:13]([NH:20][CH:21]([CH:23]=[CH:9][CH:3]1[C:2]([CH3:11])([CH3:1])[CH2:6][CH2:5][C:4]1([CH3:8])[CH3:7])[CH3:22])([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

Participants

5

Reactant 3

HCID 5462224Magnesium2×HCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamateHCID 136292612,2,5,5-Tetramethyl-1-cyclopentylmethylbromide

Product 1

HCID 70445522N-Boc-2-amino-4-(2,2,5,5-tetramethyl-1-cyclopentyl)-3-butene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,2,5,5-Tetramethyl-1-cyclopentylmethyl bromide in ether is added slowly to magnesium turnings until the Grignard reagent begins to form. The remainder of the alkyl bromide is then added and the mixture stirred until all the magnesium has dissolved. At 0° C. a solution of N-Boc-D-alaninal is then added and the mixture is stirred overnight. The reaction is quenched with 1M HCl, extracted with ether and the extracts are evaporated. The residue is dissolved in dioxane and 2M H2SO4 is added. The mixture is heated until the alcohol is dehydrated, as shown by thin layer chromatography. Water is added and the mixture is extracted with ether. The organic layer is dried over MgSO4 and evaporated to give N-Boc-2-amino-4-(2,2,5,5-tetramethyl-1-cyclopentyl)-3-butene.

Workup

  1. customto form
  2. dissolutionhas dissolved
  3. customThe reaction is quenched with 1M HCl
  4. extractionextracted with ether
  5. customthe extracts are evaporated
  6. dissolutionThe residue is dissolved in dioxane
  7. addition2M H2SO4 is added
  8. temperatureThe mixture is heated until the alcohol
  9. additionWater is added
  10. extractionthe mixture is extracted with ether
  11. dry with materialThe organic layer is dried over MgSO4
  12. customevaporated

Sources & evidence

ORD record
ord-ed69eb06730a41aea63e6b90eb7d619f
Source dataset
uspto-grants-1986_07
Patent number
US04603012

Reaction notes

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