tert-butylmethyl(3-(5-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)pyridin-2-yl)prop-2-ynyl)carbamate → tert-butyl methyl(3-(5-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)pyridin-2-yl)propyl)carbamate

HRID 626171Notes

Reaction equation

HRID 626171 reaction equation
[C:1]([O:5][C:6](=[O:33])[N:7]([CH3:32])[CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:31])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)=[CH:20][CH:19]=2)=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[CH3:32][N:7]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:31])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)=[CH:20][CH:19]=2)=[CH:13][N:12]=1)[C:6](=[O:33])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 89672875tert-butylmethyl(3-(5-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)pyridin-2-yl)prop-2-ynyl)carbamate

Product 1

HCID 121266711tert-butyl methyl(3-(5-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)pyridin-2-yl)propyl)carbamateYield 55.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney nickel (2.4 mg, 0.04 mmol, 10 mol %) was added to a solution of tert-butylmethyl(3-(5-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)pyridin-2-yl)prop-2-ynyl)carbamate (180 mg, 0.4 mmol) in 3 mL methanol at room temperature, and the reaction mixture was stirred for 1 h under hydrogen atmosphere. The nickel was filtered off and the filtrate was concentrated in vacuo to afford the desired product as a yellow solid (100 mg, 55.6% yield).

Workup

  1. filtrationThe nickel was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9b618188a1e6490a9e9e65eed5f9c801
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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