Triethylamine → HCID 131736934, compound

HRID 56435Notes

Reaction equation

HRID 56435 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.O=C1CCC(=O)N1[C:25]([O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])=[O:26]>O1CCOCC1.O.C(OCC)(=O)C>[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:25](=[O:26])[O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 120428161-Pyrrolidinecarboxylic acid, 2,5-dioxo-, 2-(trimethylsilyl)ethyl esterHCID 118036559(4R,5R)-5-Amino-2,2-dimethyloxan-4-ol

Product 1

HCID 131736934HCID 131736934, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (4R,5R)-5-amino-2,2-dimethyl-tetrahydro-2H-pyran-4-ol (550 mg, 2.40 mmol) and triethylamine (484 mg, 4.80 mmol) in dioxane (5 mL) and water (5 mL) was added 2-(trimethylsilyl)ethyl 2,5-dioxopyrrolidine-1-carboxylate (750 mg, 2.90 mmol) at room temperature. 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 concentrated, and the residue was purification by silica gel column with petroleum ether/ethyl acetate=4/1 to 1/1 to afford the title compound (360 mg, 52% for 2 steps) as a gray solid.

Workup

  1. washwashed with brine
  2. concentrationThe organic layer was concentrated
  3. custompurification by silica gel column with petroleum ether/ethyl acetate=4/1 to 1/1

Sources & evidence

ORD record
ord-05f855ef1a414262ba407faebaf3eb46
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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