Water → HCID 54076107, compound

HRID 1906649Notes

Reaction equation

HRID 1906649 reaction equation
[C:1]([NH:8][CH:9]([CH2:21][OH:22])[CH:10]=[CH:11][CH:12]1[C:16]([CH3:18])([CH3:17])[CH2:15][CH2:14][C:13]1([CH3:20])[CH3:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:23]OS(OC)(=O)=O.O>C(Cl)Cl>[C:1]([NH:8][CH:9]([CH2:21][O:22][CH3:23])[CH:10]=[CH:11][CH:12]1[C:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][C:16]1([CH3:18])[CH3:17])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6497Dimethyl SulfateHCID 54311457HCID 54311457, compound

Product 1

HCID 54076107HCID 54076107, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2,5,5-tetramethylcyclopentylmethyl bromide in ether is added slowly to magnesium turnings until the Grignard begins to form. The remainder of the alkyl bromide is then added and the mixture stirred until all the magnesium dissolved. At 0° C. a solution of N-Boc-0-methyl-D-serinal is quenched with 1M HCl, and 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 is evaporated to give N-Boc-3-amino-4-methoxy-1-(2,2,5,5-tetramethylcyclopentyl)--butene and some N-Boc-3-amino-4-hydroxy-1-(2,2,5,5-tetramethylcyclopentyl)-1-butene. This mixture is dissolved in methylene chloride and is methylated with dimethylsulfate. Water is added and the mixture is extracted with ether. The organic layer is dried over MgSO4 and is evaporated to give N-Boc-3-amino-4-methoxy-1-(2,2,5,5-tetramethylcyclopentyl)-1-butene.

Workup

  1. extractionthe mixture is extracted with ether
  2. dry with materialThe organic layer is dried over MgSO4
  3. customis evaporated

Sources & evidence

ORD record
ord-e679368f1bff453e9d53d43ba214dccd
Source dataset
uspto-grants-1987_03
Patent number
US04652676

Reaction notes

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