Lithium aluminum hydride → 1607592-18-6

HRID 712108Notes

Reaction equation

HRID 712108 reaction equation
[AlH4-].[Li+].[NH2:3][C:4]1([C:14](O)=[O:15])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1>O1CCCC1>[NH2:3][C:4]1([CH2:14][OH:15])[CH2:13][CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 70155058-amino-1,4-dioxaspiro[4.5]decane-8-carboxylic Acid

Product 1

HCID 840719951607592-18-6Yield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium tetrahydroaluminate (189 mg, 4.97 mmol) was added in portions to a solution of 8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylic acid (from Aldrich, 0.50 g, 2.5 mmol) in tetrahydrofuran (20 mL) with stirring at about 0° C. The resulting mixture was slowly warmed to room temperature and stirred overnight. Fieser workup (0.2 mL H2O, 0.2 mL 10% NaOH, 0.6 mL H2O) was performed followed by filtration through Celite and concentrated to give 0.41 g of the desired product to be used without further purifications. LCMS calculated for C9H18NO3 (M+H)+: m/z=188.1. Found: 188.0.

Workup

  1. temperatureThe resulting mixture was slowly warmed to room temperature
  2. stirringstirred overnight
  3. filtrationFieser workup (0.2 mL H2O, 0.2 mL 10% NaOH, 0.6 mL H2O) was performed followed by filtration through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c77cc72a3e2546c08e456991be82957a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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