Methyl propiolate → HCID 178498825, compound

HRID 916051Notes

Reaction equation

HRID 916051 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([N:14]=[N+:15]=[N-:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:23])[C:21]#[CH:22].CCN(C(C)C)C(C)C>[Cu]I.C1COCC1>[CH3:18][O:19][C:20]([C:21]1[N:16]=[N:15][N:14]([C@H:11]2[CH2:12][CH2:13][C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:17])[CH2:9][CH2:10]2)[CH:22]=1)=[O:23]

Participants

6

Reactant 3

HCID 13536Methyl propiolateHCID 81531DiisopropylethylamineHCID 178418853HCID 178418853, compound

Product 1

HCID 178498825HCID 178498825, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a THF (30 ml) solution under Ar of (cis-4-azido-cyclohexyl)carbamic acid tert-butyl ester (3.00 g) and propiolic acid methyl ester (1.05 g) were added CuI (2.38 g) and DIPEA (3.18 ml). The resulting slurry was stirred at RT over night. After dilution with EtOAc (200 ml) the mixture was washed with H2O (200 ml), dried over Na2SO4 and the solvent was evaporated. Chromatography (silica, CH2Cl2/MeOH 95:5) yielded 2.63 g (65%) of product. White crystals. MS 325.4 (95, [M+H]+), 269.4 (100, [M−tBu].+).

Workup

  1. washAfter dilution with EtOAc (200 ml) the mixture was washed with H2O (200 ml)
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-70ca05cbca7c4c4fa94de4cb82dac050
Source dataset
uspto-grants-2007_09
Patent number
US07268154B2

Reaction notes

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