Triethylamine → HCID 131736938, compound

HRID 56440Notes

Reaction equation

HRID 56440 reaction equation
[NH2:1][C@H:2]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[CH2:4][C@@H:3]1[OH:10].C(N(CC)CC)C.O1CCOCC1.O=C1CCC(=O)N1[C:31]([O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])=[O:32]>C(OCC)(=O)C.O>[OH:10][C@H:3]1[CH2:4][C:5]([CH3:9])([CH3:8])[O:6][CH2:7][C@@H:2]1[NH:1][C:31](=[O:32])[O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 120428161-Pyrrolidinecarboxylic acid, 2,5-dioxo-, 2-(trimethylsilyl)ethyl esterHCID 118036455(4S,5S)-5-amino-2,2-dimethyl-tetrahydropyran-4-ol

Product 1

HCID 131736938HCID 131736938, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4S,5S)-5-amino-2,2-dimethyl-tetrahydro-2H-pyran-4-ol (1.1 g, 4.0 mmol) and triethylamine (1.1 mL, 8.0 mmol) in a mixed solvent of dioxane (5 mL) and water (5 mL) at room temperature was added 2-(trimethylsilyl)ethyl 2,5-dioxopyrrolidine-1-carboxylate (1.2 g, 4.8 mmol). The reaction mixture was stirred at room temperature for 4 hours. After that, the solution was diluted with ethyl acetate and washed with brine. The organic layer was separated and concentrated. The resulting residue was purified by silica gel chromatography using petroleum ether/ethyl acetate=4/1 to 1/1 as the eluent to afford the title compound (1.0 g, 86% for 2 steps) as a yellow oil.

Workup

  1. washwashed with brine
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fa1c4eb34b68477a85de154b8abe9262
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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