1,4-Dioxane hydrochloride → HCID 117697385, compound

HRID 1778484Notes

Reaction equation

HRID 1778484 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][O:6][C@@H:7]1[CH2:13][C@H:12]2[N:14](C(OC(C)(C)C)=O)[C@@H:8]1[CH2:9][O:10][CH2:11]2)[CH3:2].Cl.O1CCOCC1>C(Cl)Cl>[CH:12]12[NH:14][CH:8]([CH:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:22])[CH2:13]1)[CH2:9][O:10][CH2:11]2

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 117700211HCID 117700211, compound

Product 1

HCID 117697385HCID 117697385, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,5R,6R)-tert-butyl 6-(2-ethoxy-2-oxoethoxy)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate 50a (racemic, 200 mg, 0.63 mmol) in DCM (10 mL) was added HCl/dioxane (2 mL, 7 M). The resulting mixture was stirred at room temperature for 2 h. The organic solvent was removed in vacuo to give the compound 50b (150 mg, 94%). MS: calc'd (MH+) 216, measured (MH+) 216; 1H NMR (CDCl3, 400 MHz): 4.28 (m, 8H), 3.79 (m, 1H), 3.70 (s, 1H), 3.57 (d, J=12.4 Hz, 1H), 2.50 (m, 1H), 2.31 (m, 1H), 1.28 (m, 3H).

Workup

  1. customThe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-f80a7add113f455c808fb7b791831e87
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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