Triethylamine → tert-Butyl{(3S,5S,6R)-2-[(2-hydroxy-3-methoxy-3-methylbutyl)imino]-6-methyl-5-phenylpiperidin-3-yl}carbamate

HRID 2179469Notes

Reaction equation

HRID 2179469 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].[NH2:23][CH2:24][CH:25]([OH:31])[C:26]([O:29][CH3:30])([CH3:28])[CH3:27].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:23][CH2:24][CH:25]([OH:31])[C:26]([O:29][CH3:30])([CH3:28])[CH3:27])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 552850861-Amino-3-methoxy-3-methylbutan-2-olHCID 131732078tert-Butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate

Product 1

HCID 137187577tert-Butyl{(3S,5S,6R)-2-[(2-hydroxy-3-methoxy-3-methylbutyl)imino]-6-methyl-5-phenylpiperidin-3-yl}carbamate

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To as solution of tert-butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate (150 mg, 0.47 mmol) in ethanol (4.7 mL) was added 1-amino-3-methoxy-3-methylbutan-2-ol (156 mg, 1.17 mmol), mercury (II) chloride (165 mg, 0.61 mmol), and triethylamine (163 μL, 1.17 mmol). The mixture was stirred 20 min, and then concentrated, giving the crude title compound. MS 420.4 (M+1).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-1ff3da9493d04ea6b3f41e0518a0f6f6
Source dataset
uspto-grants-2015_06
Patent number
US09067941B2

Reaction notes

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