Aluminium lithium hydride → HCID 23047401, compound

HRID 2107082Notes

Reaction equation

HRID 2107082 reaction equation
[CH:1]([C:4]1[N:8]2[CH:9]=[CH:10][C:11]3[C:16]([C:7]2=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1[C:23](OCC)=[O:24])=[CH:15][CH:14]=[CH:13][CH:12]=3)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:24][CH2:23][C:5]1[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]2[C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23047420HCID 23047420, compound

Product 1

HCID 23047401HCID 23047401, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 3-isopropyl-1-phenylpyrrolo-[2,1-a]isoquinoline-2-carboxylate (6.25 g) in anhydrous diethyl ether (100 ml) was added to a stirred suspension of lithium aluminum hydride (2.7 g) in diethyl ether (160 ml) at -2° C. under an atmosphere of argon. The mixture was stirred at between -5° and 0° C. for 5 hours and then the reaction mixture was quenched by the dropwise addition of ethyl acetate (50 ml), followed by dilute hydrochloric acid (100 ml; 1N), maintaining the temperature below 10° C. The organic phase was then separated. The aqueous phase was extracted with dichloromethane (2×150 ml) and the organic solutions were combined, washed with brine (300 ml), dried over magnesium sulphate and evaporated, to give 2-hydroxymethyl-3-isopropyl-1-phenylpyrrolo[2,1-a]-isoquinoline (5.1 g) in the form of a sticky yellow solid. [N.M.R. (in DMSO-d6): 1.48 (6H, d, J= 7 Hz), 3.65 (1H, septet, J=7 Hz), 4.3 (2H, d, J=4 Hz), 4.5 (1H, broad t, J=4 Hz), 6.85 (1H, d, J=8 Hz), 7.0-7.7 (9H, m), and 8.1 (1H, d, J=8 Hz)].

Workup

  1. customthe reaction mixture was quenched by the dropwise addition of ethyl acetate (50 ml)
  2. temperaturemaintaining the temperature below 10° C
  3. customThe organic phase was then separated
  4. extractionThe aqueous phase was extracted with dichloromethane (2×150 ml)
  5. washwashed with brine (300 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-08da3ef4eb2e4c4592ebdcbb2355b38a
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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