tert-butyl methyl(3-(4-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)-phenyl)prop-2-ynyl)carbamate → tert-butyl methyl(3-(4-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)-phenyl)propyl)carbamate

HRID 626174Notes

Reaction equation

HRID 626174 reaction equation
[CH3:1][N:2]([CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:33])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]>[Ni].CO>[CH3:1][N:2]([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:33])[C:20]2[CH:21]=[CH:22][C:23]([O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[CH:24][CH:25]=2)=[CH:15][CH:14]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 1

HCID 121266719tert-butyl methyl(3-(4-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)-phenyl)prop-2-ynyl)carbamate

Product 1

HCID 121266705tert-butyl methyl(3-(4-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)-phenyl)propyl)carbamateYield 80.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A flask was charged with tert-butyl methyl(3-(4-(4-(tetrahydro-2H-pyran-2-yloxy)benzoyl)phenyl)prop-2-ynyl)carbamate (450 mg, 1 mmol), Riney Ni (0.2 eq), and 20 mL of methanol. The mixture was stirred under hydrogen at room temperature and atmospheric pressure for 2 h. After complete conversion (TLC monitoring), the catalyst was filtered off through a pad of celite, and washed with EtOAc. The filtrate was concentrated under reduced pressure to give the product (364 mg, 80% yield).

Workup

  1. filtrationAfter complete conversion (TLC monitoring), the catalyst was filtered off through a pad of celite
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4906ae56f18c45b7973b21c5cd239719
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…