Aluminium lithium hydride → HCID 67974752, compound

HRID 706543Notes

Reaction equation

HRID 706543 reaction equation
C(O[C:6]([N:8]1[CH2:11][C:10]2([CH2:14][N:13]([CH2:15][CH2:16][OH:17])[CH2:12]2)[CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:6][N:8]1[CH2:11][C:10]2([CH2:14][N:13]([CH2:15][CH2:16][OH:17])[CH2:12]2)[CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67974147HCID 67974147, compound

Product 1

HCID 67974752HCID 67974752, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl-6-(2-hydroxyethyl)-2,6-diazaspiro[3.3]heptane-2-carboxylate (0.620 g, 2.56 mmol) was dissolved in dry THF (13 mL) and chilled to 0° C. Lithium aluminum hydride (7.68 mL, 7.68 mmol, 1M in THF) was added by syringe. Once addition was complete, the mixture was brought to reflux for 16 hours. The reaction was cooled to 0° C., quenched with 291 μL of water, 291 μL of 15% aq. NaOH, and 873 μL of water, stirred vigorously for two hours, and then filtered. The filtrate was concentrated under reduced pressure to give 268 mgs (67%) of the title compound.

Workup

  1. additionOnce addition
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with 291 μL of water, 291 μL of 15% aq. NaOH, and 873 μL of water
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5766f2ff0f5c4eb4a4bfbc1b8b47217b
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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