Aluminium lithium hydride → 2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]ethan-1-amine

HRID 76224Notes

Reaction equation

HRID 76224 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH2:18][C:19]#[N:20])[CH2:17][C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]2([CH2:18][CH2:19][NH2:20])[CH2:17][C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[O:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 683144862-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile

Product 1

HCID 683140582-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]ethan-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (500 mg, 1.8 mmol) in anhydrous ether (30 ml) at 0° C. was added dropwise LAH (1.0 M in Et2O, 3.7 ml, 3.7 mmol). The reaction was then warmed up to room temperature. After 2 h the reaction was quenched with 1 ml H2O, 0.2 ml 15% NaOH and then 1 ml H2O. The reaction mixture was extracted with Et2O (3×30 ml), dried over NA2SO4 and concentrated to give 2-[(9R)-9-(4-fluorophenyl)-6-oxaspiro[4.5]decan-9-yl]ethan-1-amine as an yellow oil, which used without further purification (500 mg, 100%, m/z 277.2 [M+H]+ observed).

Workup

  1. customAfter 2 h the reaction was quenched with 1 ml H2O, 0.2 ml 15% NaOH
  2. extractionThe reaction mixture was extracted with Et2O (3×30 ml)
  3. customdried over NA2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dd87759fb417408082c3af03e6ff69bf
Source dataset
uspto-grants-2014_09
Patent number
US08835488B2

Reaction notes

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