HCID 18782843, compound → HCID 18782848, compound

HRID 1420791Notes

Reaction equation

HRID 1420791 reaction equation
[CH2:1]([CH:3]1[CH:8]([C:9]#[N:10])[CH2:7][CH:6]2[CH2:11][CH:4]1[C:5]2([CH3:13])[CH3:12])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([CH:3]1[CH:8]([CH2:9][NH2:10])[CH2:7][CH:6]2[CH2:11][CH:4]1[C:5]2([CH3:12])[CH3:13])[CH3:2]

Participants

4

Reactant 2

HCID 18782843HCID 18782843, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18782848HCID 18782848, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Ethyl-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carbonitrile (288 mg, 1.65 mmol) was dissolved in anhydrous THF (10 ml) under an atmosphere of dry N2. To the reaction was added a 1.0 M solution of lithium aluminum hydride (4.0 ml) in THF. The reaction was stirred at ambient temperature for 16 hr and was then quenched by the sequential slow addition of 152 μl of water, 152 μl of 15% NaOH and finally 460 μl of water. The reaction was stirred for an additional 2 hr after which time it was filtered and the filter cake was washed with CH 2Cl2. The combined filtrate was concentrated under vacuum to give 267 mg of the titled compound: 1H NMR (CD3OD) 6 2.73 (dd, J=4.6,12.2 Hz, 1H), 2.41 (dd, J=9.5, 12.2 Hz, 1H), 2.32 (m, 1H), 2.19 (m, 1H), 1.98 (m, 1H), 1.91 (m, 1H), 1.74 (m, 1H), 1.28-1.57 (m, 4H), 1.20 (s, 3H), 0.99 (s, 3H), 0.89 (t, J=7.2 Hz, 3H), 0.74 (d, J=9.6 Hz, 1H).

Workup

  1. customwas then quenched by the sequential slow addition of 152 μl of water, 152 μl of 15% NaOH and finally 460 μl of water
  2. stirringThe reaction was stirred for an additional 2 hr after which time it
  3. filtrationwas filtered
  4. washthe filter cake was washed
  5. concentrationThe combined filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-fd9813b7cd6e4844beae5df1fcacd262
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Reaction notes

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