Hydrogen chloride-ethyl acetate → HCID 86702796, compound

HRID 1425914Notes

Reaction equation

HRID 1425914 reaction equation
[C@@H:1]12[N:7](C(OC(C)(C)C)=O)[C@@H:4]([CH2:5][CH2:6]1)[CH:3]([C:15]([O:17][CH3:18])=[O:16])[CH:2]2[C:19]([O:21][CH3:22])=[O:20].Cl.CCOC(C)=O>CCOC(C)=O>[C@@H:4]12[NH:7][C@@H:1]([CH2:6][CH2:5]1)[CH:2]([C:19]([O:21][CH3:22])=[O:20])[CH:3]2[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86702795HCID 86702795, compound

Product 1

HCID 86702796HCID 86702796, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(1R,4S)-7-tert-butyl 2,3-dimethyl 7-azabicyclo[2.2.1]heptane-2,3,7-tricarboxylate (XLVIII) (3.28 g, 10.49 mmol) was dissolved in EtOAc (20 mL) and treated with 1M HCl/EtOAc (20 mL) and stirred for 15 minutes at room temperature. The solvent was removed under vacuum and the oily residue triturated with Et2O to give (1R,4S)-dimethyl 7-azabicyclo[2.2.1]heptane-2,3-dicarboxylate (LXIX) as a light pink solid (2.46 g, 9.86 mmol, 94% yield). 1H NMR (DMSO-d6) (two isomers in a 4/1 ratio) δ ppm [1.41-1.53 (m, 2nd isomer), 1.77-1.83 (m, 1st isomer), 2H], [1.63-1.72 (m, 2nd isomer), 1.93-2.02 (m, 1st isomer), 2H], [3.16 (d. J=6 Hz, 2nd isomer), 3.38 (brs, 1st isomer), 2H], [3.57 (s, 1st isomer), 3.62 (s, 2nd isomer), 6H], [4.34 (brs, 1st isomer), 4.40 (d, J=4 Hz, 2nd isomer), 2H], [9.68 (brs, 1st isomer), 9.92 (brs, 2nd isomer, 2H]. ESIMS found for C10H15NO4 m/z 214 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe oily residue triturated with Et2O

Sources & evidence

ORD record
ord-8e050b7a839246288c45f70a98afb077
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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