Aluminium lithium hydride → 8-Benzyl-3,8-diazabicyclo[3.2.1]octane

HRID 2200365Notes

Reaction equation

HRID 2200365 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C@@H:19]2[CH2:20][CH2:21][C@H:15]1[C:16](=O)[NH:17][CH2:18]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH2:7]([N:14]1[CH:19]2[CH2:20][CH2:21][CH:15]1[CH2:16][NH:17][CH2:18]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69892414HCID 69892414, compound

Product 1

HCID 120798988-Benzyl-3,8-diazabicyclo[3.2.1]octaneYield 91%

Conditions

Temperature
67.5 °C

Procedure

To a stirred suspension of lithium aluminium hydride in tetrahudrofuran (30 ml) at 0° C. was added a solution of (1S,5R)-8-benzyl-3,8-diazabicyclo[3.2.1]octan-2-one (prepared according to the procedure reported in US200565178 A1, 1.0 g, 4.62 mmol) in 15 ml tetrahudrofuran (15 ml) under nitrogen atmosphere. The reaction mixture was allowed to stir at 25° C. for 2 h and at 65-70° C. for 1 h. The reaction mixture was cooled to 0° C. and slowly quenched with 15% aqueous Sodium hydroxide (5 ml). The reaction mixture was diluted with ethyl acetate (50 ml) and filtered through a celite bed. The filtrate was dried over sodium sulphate and concentrated under reduced pressure to obtain the title compound (0.85 g, 91%).

Workup

  1. customprepared
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customslowly quenched with 15% aqueous Sodium hydroxide (5 ml)
  4. additionThe reaction mixture was diluted with ethyl acetate (50 ml)
  5. filtrationfiltered through a celite bed
  6. dry with materialThe filtrate was dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c632b94d20848e89a951d365280d40b
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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