Triethylamine → tert-Butyl{(3S,5S,6R)-6-methyl-5-phenyl-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]piperidine-3-yl}carbamate

HRID 2179466Notes

Reaction equation

HRID 2179466 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[NH:10][C:9]1=S)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:24][CH2:25][CH:26]([OH:32])[CH2:27][C:28]([F:31])([F:30])[F:29].C(N(CC)CC)C>C(O)C.[Hg](Cl)Cl>[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[NH:10][C:9]1=[N:24][CH2:25][CH:26]([OH:32])[CH2:27][C:28]([F:31])([F:30])[F:29])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 862389211-Amino-4,4,4-trifluorobutan-2-ol hydrochlorideHCID 131732078tert-Butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate

Product 1

HCID 137231131tert-Butyl{(3S,5S,6R)-6-methyl-5-phenyl-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]piperidine-3-yl}carbamate

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate (75 mg, 0.23 mmol) in ethanol (2.3 mL) was added 1-amino-4,4,4-trifluorobutan-2-ol hydrochloride (105 mg, 0.59 mmol), mercury(II) chloride (83 mg, 0.30 mmol), and triethylamine (78 μL, 0.56 mmol). The mixture was stirred 30 min, filtered, and then concentrated, giving the crude title compound. MS 430.3 (M+1).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-baedbb0cd2f94c47ac437184a04e63ca
Source dataset
uspto-grants-2015_06
Patent number
US09067941B2

Reaction notes

Loading…