Aluminium lithium hydride → Trv-0109662

HRID 626493Notes

Reaction equation

HRID 626493 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C@@:13]1([CH2:23][C:24]#[N:25])[CH2:22][C:17]2([CH2:21][CH2:20][CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1>CCOCC>[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C@@:13]1([CH2:23][CH2:24][NH2:25])[CH2:22][C:17]2([CH2:21][CH2:20][CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68314099(R)-2-(9-(Pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl)acetonitrile

Product 1

HCID 68314401Trv-0109662Yield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LAH (1M in Et2O, 20 ml, 20 mmol) was added to a solution of 2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (2.56 g, 10 mmol) in Et2O (100 ml, 0.1M) at 0° C. under N2. The resulting mix was stirred and allowed to warm to room temperature. After 2 h, LCMS showed the reaction had completed. The reaction was cooled at 0° C. and quenched with water (1.12 ml), NaOH (10%, 2.24 ml) and another 3.36 ml of water. Solid was filtered and filter pad was washed with ether (3×20 ml). The combined organic was dried and concentrated to give 2-[(9R)-9-(Pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]ethan-1-amine (2.44 g, 94% yield, m/z 260.6 [M+H]+ observed) as a light amber oil.

Workup

  1. additionThe resulting mix
  2. temperatureThe reaction was cooled at 0° C.
  3. customquenched with water (1.12 ml), NaOH (10%, 2.24 ml)
  4. filtrationSolid was filtered
  5. filtrationfilter pad
  6. washwas washed with ether (3×20 ml)
  7. customThe combined organic was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a4319d9873cf4ad2b799a38a1bf09f9d
Source dataset
uspto-grants-2016_04
Patent number
US09309234B2

Reaction notes

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