Triethylamine → HCID 53742937, compound

HRID 713440Notes

Reaction equation

HRID 713440 reaction equation
[NH:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>O1CCCC1>[C:23]([O:22][C:20](=[O:21])[CH2:19][N:1]1[CH2:10][CH2:9][CH:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][CH2:2]1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 424914Methyl isonipecotate

Product 1

HCID 53742937HCID 53742937, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl isonipecotate (10.0 g, 69.8 mmol) and triethylamine (19.5 mL, 140 mmol) in tetrahydrofuran (200 mL) was added tert-butyl bromoacetate (10.3 mL, 69.8 mmol). The solution was heated at reflux for 24 h, concentrated under reduced pressure and purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0, methanol: dichloromethane, 1:99 to 5:95) to provide the title compound (18 g). 1H NMR (400 MHz, CDC3) δ 3.61 (s, 3H), 3.04 (s, 2H), 2.84 (d, J=11.5 Hz, 2H), 2.12-2.31 (m, 3H), 1.64-1.91 (m, 4H), 1.39 (s, 9H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 24 h
  3. concentrationconcentrated under reduced pressure
  4. custompurified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0, methanol: dichloromethane, 1:99 to 5:95)

Sources & evidence

ORD record
ord-2942c170bada49f8818eb03365202b3a
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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