HCID 71116097, compound → HCID 51382709, compound

HRID 1423854Notes

Reaction equation

HRID 1423854 reaction equation
[N+:1]([CH2:4][C@H:5]1[CH2:14][CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6]1)([O-])=O>CCO.[Pd]>[O:8]1[C:7]2([CH2:12][CH2:13][CH2:14][C@H:5]([CH2:4][NH2:1])[CH2:6]2)[O:11][CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 71116097HCID 71116097, compound

Product 1

HCID 51382709HCID 51382709, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-7-(nitromethyl)-1,4-dioxaspiro[4.5]decane (5.00 g, 24.9 mmol) in EtOH (150 mL) in a 1000 mL Parr bottle was flushed with nitrogen before Pd/C (1.32 g, 1.24 mmol) was added in one portion under nitrogen. The reaction flask was evacuated, charged with hydrogen (56 psi), and shaken for 19 h on the Parr shaker. The reaction mixture was filtered through celite under a stream of nitrogen, and the filtrate was concentrated to afford the crude title compound (4.37 g, 103% crude yield) which was used without further purification.

Workup

  1. additionwas added in one portion under nitrogen
  2. customThe reaction flask was evacuated
  3. additioncharged with hydrogen (56 psi)
  4. filtrationThe reaction mixture was filtered through celite under a stream of nitrogen
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e3780bda865b4788884050f1b39d1033
Source dataset
uspto-grants-2015_01
Patent number
US08927585B2

Reaction notes

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