Benzylamine → HCID 69028019, compound

HRID 459963Notes

Reaction equation

HRID 459963 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@H:5]([C:7](Cl)=[O:8])[C@@H:4]([CH3:10])[O:3]1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[CH2:12]([NH:19][C:7]([C@@H:5]1[C@@H:4]([CH3:10])[O:3][C:2]([CH3:11])([CH3:1])[O:6]1)=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 45081486(4S,5R)-2,2,5-Trimethyl-1,3-dioxolane-4-carbonyl chloride

Product 1

HCID 69028019HCID 69028019, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A flask was charged with 70 mL dry tetrahydrofuran, 3.17 g (17.7 mmol) (4S,5R)-2,2,5-trimethyl[1,3]dioxolane-4-carbonyl chloride, and the solution was cooled in a 0° C. bath. To this solution, 3.48 mL (31.9 mmol) benzyl amine was slowly added, and a precipitate formed immediately. The reaction mixture was stirred for 1 hour at 0° C. and 1 hour at room temperature. The reaction mixture was filtered through Celite to remove salts, and the tetrahydrofuran was removed under reduced pressure giving 4.41 g (100%) of the title compound as a yellow oil. No further purification was necessary. MS (APCI) (m+1)/z 250.1.

Workup

  1. customa precipitate formed immediately
  2. filtrationThe reaction mixture was filtered through Celite
  3. customto remove salts
  4. customthe tetrahydrofuran was removed under reduced pressure

Sources & evidence

ORD record
ord-ac013fdf325946b98f8bbbd88bca221d
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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