Tert-Butylamine → HCID 19082433, compound

HRID 1289911Notes

Reaction equation

HRID 1289911 reaction equation
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[CH2:9]([O:8][C:7]1[C:6](=[O:11])[C:5](=[O:12])[C:4]=1[NH:17][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:10]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 123228Diethyl squarate

Product 1

HCID 19082433HCID 19082433, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 5.81 g (34 mmol) of 3,4-diethoxy-3-cyclobutene-1,2-dione and 50 mL of THF was added 2.9 g (34 mmol) of tert-butyl amine. After stirring at room temperature for 12 hours, the reaction mixture was evaporated to a yellow oil. Flash chromatography on silica gel, eluting with 0 to 5% MeOH/CH2Cl2 gave 6.2 g (34 mmol, a 100% yield) of the title compound as a white solid: mp: 80°-82° C.; 1H NMR: (300 MHz, DMSO-d6): δ1.30-1.62 (m, 12H), 4.70-4.93 (m, 2H), 5.50-6.42 (brm, 1H); IR (KBr, cm-1): 3214w, 3144m, 3071w, 2973m, 2941m, 1794m, 1702s, 1606s, 1577s, 1500-1442brs; MS (CI) m/z (relative intensity): 198 (M+H, 100); Anal. Calcd. for C10H15NO3 : C, 60.90; H, 7.67; N, 7.10. Found: C, 61.03; H, 7.66; N, 6.98.

Workup

  1. customthe reaction mixture was evaporated to a yellow oil
  2. washFlash chromatography on silica gel, eluting with 0 to 5% MeOH/CH2Cl2
  3. customgave 6.2 g (34 mmol

Sources & evidence

ORD record
ord-54fa327c094b4ff9a796eba931ab0656
Source dataset
uspto-grants-1998_05
Patent number
US05750574

Reaction notes

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