Ethanol → HCID 68459877, compound

HRID 1960339Notes

Reaction equation

HRID 1960339 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([S:14][C:15]1([CH2:25][N+:26]([O-])=O)[CH2:24][CH2:23][C:18]2([O:22][CH2:21][CH2:20][O:19]2)[CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O)C.O>O1CCCC1>[CH2:7]([S:14][C:15]1([CH2:25][NH2:26])[CH2:24][CH2:23][C:18]2([O:19][CH2:20][CH2:21][O:22]2)[CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59136148HCID 59136148, compound

Product 1

HCID 68459877HCID 68459877, compoundYield 123.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of lithium aluminum hydride (2.63 g) and tetrahydrofuran (50 mL) was added a solution of 8-(benzylthio)-8-(nitromethyl)-1,4-dioxaspiro[4.5]decane (8.96 g) in tetrahydrofuran (80 mL) over 1 hr at room temperature, and the reaction mixture was stirred at room temperature for 30 min. Ethanol (15 mL) and water (10 mL) was successively added, and the resulting inorganic salt was removed by filtration. The filtrate was concentrated, and the residue was dissolved in ethyl acetate. The solution was dried (MgSO4), and concentrated to give 1-[8-(benzylthio)-1,4-dioxaspiro[4.5]dec-8-yl]methanamine (10.02 g) as a crude oil.

Workup

  1. customthe resulting inorganic salt was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. dry with materialThe solution was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e660aa0424034f21a404d610160fcd5f
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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