methyl-{3-[4-((R)-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl-carbamoyl)-thiazol-2-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester → methyl-{3-[4-((R)-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl-carbamoyl)-thiazol-2-yl]-propyl}-carbamic acid tert-butyl ester

HRID 470721Notes

Reaction equation

HRID 470721 reaction equation
[C:1]([O:5][C:6](=[O:31])[N:7]([CH3:30])[CH2:8][C:9]#[C:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:29])[N:17]([CH3:28])[C@H:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][CH2:20][CH2:19]2)[N:15]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:31])[N:7]([CH3:30])[CH2:8][CH2:9][CH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:29])[N:17]([CH3:28])[C@H:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][CH2:20][CH2:19]2)[N:15]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 67252656methyl-{3-[4-((R)-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl-carbamoyl)-thiazol-2-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester

Product 1

HCID 67252275methyl-{3-[4-((R)-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl-carbamoyl)-thiazol-2-yl]-propyl}-carbamic acid tert-butyl esterYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl-{3-[4-((R)-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl-carbamoyl)-thiazol-2-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester (0.176 g, 0.4 mmol) in methanol (3 mL) was pumping through Pd/C cartridge using H-Cube apparatus (50° C., 80 bar, 1 mL/min.). The solvent was then evaporated under reduce pressure to give methyl-{3-[4-((R)-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl-carbamoyl)-thiazol-2-yl]-propyl}-carbamic acid tert-butyl ester (0.133 g, 75%), which can be used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ=7.54 (s, 1H (conformers)), 7.03-6.87 (m, 4H), 5.54-5.46 (m, 1H (conformers)), 3.12-2.98 (m, 2H), 2.83-2.71 (m, 2H (conformers)), 2.63 (s, 3H (conformers)), 2.61-2.51 (m, 5H), 2.04-1.56 (m, 6H), 1.20 (s, 9H (conformers)). MS: m/z=444 (M+1).

Workup

  1. customapparatus (50° C., 80 bar, 1 mL/min.)
  2. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-924a53eeec0848ac8fc4297cc1a54a9c
Source dataset
uspto-grants-2014_01
Patent number
US08629286B2

Reaction notes

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