Aluminium lithium hydride → HCID 68576757, compound

HRID 273071Notes

Reaction equation

HRID 273071 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:24]#[N:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[O:1]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3([CH2:24][NH2:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68575604HCID 68575604, compound

Product 1

HCID 68576757HCID 68576757, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-[4-(3-[1,4]Oxazepan-4-yl-propoxy)-phenyl]-tetrahydro-pyran-4-carbonitrile (900 mg, 26 mmol) was dissolved in THF (5 ml) and cooled to 0° C. under nitrogen. Lithium aluminium hydride (1M in EtO2, 7.8 ml, 78 mmol) was added dropwise and left to stir for 10 minutes before heating to reflux for 18 hours. The solution was cooled to 0° C. before quenching with water (0.78 ml), followed by sodium hydroxide (2M, 0.78 ml) and finally water (2.4 ml). The resulting slurry was filtered through Arbocel®, washing through with DCM (2×10 ml). The filtrate was concentrated in vacuo to afford the title compound as a colourless oil (650 mg, 72%). HRMS ESI+ m/z 349.2480 [MH]+.

Workup

  1. waitleft
  2. temperaturebefore heating
  3. temperatureto reflux for 18 hours
  4. temperatureThe solution was cooled to 0° C.
  5. custombefore quenching with water (0.78 ml)
  6. filtrationThe resulting slurry was filtered through Arbocel®
  7. washwashing through with DCM (2×10 ml)
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-37e00b3786d247bda780b5e909c0354f
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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