Aluminium lithium hydride → HCID 58189218, compound

HRID 1423138Notes

Reaction equation

HRID 1423138 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28](=O)[CH2:29][CH2:30][C:31](OCC)=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86652000HCID 86652000, compound

Product 1

HCID 58189218HCID 58189218, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of intermediate (S)-ethyl 4-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-4-oxobutanoate (124 mg, 0.25 mmol) in THF (2 mL) was treated with a 1 N THF solution of lithium aluminum hydride (1.0 mL, 1.0 mmol) and stirred for 1 h. After this time the reaction mixture was quenched with ice water (500 μL) followed by a 5% NaOH solution (500 μL) and solid MgSO4. The material was dissolved in EtOAc, filtered and evaporated to afford the title compound as a burgundy colored oil (77 mg. 70%). LC/MS (Method A) 5.22 min, [M+1]+ 439.

Workup

  1. customAfter this time the reaction mixture was quenched with ice water (500 μL)
  2. dissolutionThe material was dissolved in EtOAc
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-91f7dade942a4237b2d9e84de7954249
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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