Aluminium lithium hydride → HCID 67919528, compound

HRID 1762130Notes

Reaction equation

HRID 1762130 reaction equation
[C:1]([C:3]1([NH:20][CH2:21][CH:22]=[CH2:23])[CH2:12][CH:11]2[N:6]([CH2:7][CH2:8][C:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[O:13][C:10]=32)[CH2:5][CH2:4]1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.CCOCC>[NH2:2][CH2:1][C:3]1([NH:20][CH2:21][CH:22]=[CH2:23])[CH2:12][CH:11]2[N:6]([CH2:7][CH2:8][C:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[O:13][C:10]=32)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67919635HCID 67919635, compound

Product 1

HCID 67919528HCID 67919528, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.325 grams (1.11 mmol) of (2RS,12bSR)-2-cyano-2-(2-propenylamino)-1,3,4,6,7,12b-hexahydro-2H-benzofuro[2,3-a]quinolizine in 7 milliliters of tetrahydrofuran is added to a solution of 0.084 gram (2.22 mmol) of lithium aluminum hydride in 60 milliliters of ether which has been cooled to 0° C. The reaction mixture is stirred for 1.5 hours and then quenched with water. The resulting mixture is filtered through a pad of celite and the pad then washed with methanol and methylene chloride. The filtrate is dried over sodium sulfate, then filtered and concentrated to obtain (2RS,12bSR)-2-aminomethyl-2-(2-propenylamino)-1,3,4,6,7,12b-hexahydro-2H-benzofuro[2,3-a]quinolizine.

Workup

  1. customquenched with water
  2. filtrationThe resulting mixture is filtered through a pad of celite
  3. washthe pad then washed with methanol and methylene chloride
  4. dry with materialThe filtrate is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e439f69b40c445e3afd97f3f2381afbf
Source dataset
uspto-grants-1989_05
Patent number
US04831035

Reaction notes

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