Diisopropylethylamine → HCID 178457232, compound

HRID 25584

Reaction equation

HRID 25584 reaction equation
[CH2:1]([N:4]([CH3:16])[CH2:5][C:6]#[C:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.[CH:26]1[C:31]([O:32][C:33](Cl)=[O:34])=[CH:30][CH:29]=[C:28]([Cl:36])[CH:27]=1>O1CCOCC1.C([O-])(O)=O.[Na+].CCOCC>[Cl:36][C:28]1[CH:29]=[CH:30][C:31]([O:32][C:33](=[O:34])[N:14]([C@H:11]2[CH2:12][CH2:13][C@H:8]([C:7]#[C:6][CH2:5][N:4]([CH2:1][CH:2]=[CH2:3])[CH3:16])[CH2:9][CH2:10]2)[CH3:15])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178457231HCID 178457231, compound

Product 1

HCID 178457232HCID 178457232, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 23682952Ether sodium bicarbonateSolvent

Procedure

A solution of 66 mg (0.3 mmol) of trans-{4-[3-(Allyl-methyl-amino)-prop-1-ynyl]-cyclohexyl}-methyl-amine in 0.3 ml dioxane was treated with 0.103 ml (0.6 mmol; 2 equivalents) Huenig's base and dropwise with a solution of 0.042 ml (0.27 mmol) 4-chlorophenylchloroformate in 0.16 ml dioxane (during 10 min). After 5 min at RT, the mixture was dissolved in aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried over Na2SO4 and evaporated. Flash column chromatography on silica gel with CH2Cl2/MeOH (99:1 to 97:3) yielded 68 mg (61%) of trans-{4-[3-(Allyl-methyl-amino)-prop-1-ynyl]-cyclohexyl}-methyl-carbamic acid 4-chloro-phenyl ester, MS: 375 (MH+, 1Cl).

Workup

  1. dry with materialThe organic phase was dried over Na2SO4
  2. customevaporated

Sources & evidence

ORD record
ord-e00da6cf44d6447186086da1eba9ec4a
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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