Aluminium lithium hydride → HCID 23627746, compound

HRID 1423124Notes

Reaction equation

HRID 1423124 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[CH2:7][C@@H:6]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:25]([C@H:6]1[CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:12]=2)[CH2:9][CH2:10][N:5]1[CH2:4][CH2:3][OH:2])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23627745HCID 23627745, compound

Product 1

HCID 23627746HCID 23627746, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-acetic acid methyl ester (110 mg, 0.25 mmol) in THF (2 mL) at room temperature was treated with a 1 N THF solution of lithium aluminum hydride (750 μL, 0.75 mmol) and allowed to stir for 12 h. The reaction mixture was quenched with an aqueous 15% NaOH solution (250 μL) followed by water (250 μL) and THF (2 mL). The reaction mixture was then treated with MgSO4, filtered, and evaporated. The residue was then dissolved in EtOAc (3 mL), retreated with MgSO4, filtered, and evaporated to afford the title compound as an oil (75 mg, 73%). 1H NMR (CDCl3) 7.33-7.20 (m, 5H), 6.75 (d, J=8.6, 1H), 6.40 (d, J=2.6, 1 H), 6.34 (dd, J=8.6, 2.9, 1H), 4.67-4.64 (m, 1H), 3.78 (s, 3H), 3.76-3.65 (m, 2H), 3.22-2.74 (m, 12H), 1.88-1.67 (m, 6H), 1.62-1.58 (m, 2H). 13C NMR 148.5, 146.5, 144.7, 139.6, 129.5 (CH), 128.8 (CH), 126.5 (CH) 113.4 (CH), 108.1 (CH), 106.5 (CH), 80.5 (CH), 61.6 (CH), 58.1 (CH2), 56.9 (CH3), 55.5 (CH2), 53.9 (CH2), 49.7 (CH2), 48.4 (CH2), 33.0 (CH2), 33.0 (CH2), 24.2 (CH2). LC/MS (Method A) 4.81 min, [M+1]+ 411.

Workup

  1. customThe reaction mixture was quenched with an aqueous 15% NaOH solution (250 μL)
  2. additionThe reaction mixture was then treated with MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue was then dissolved in EtOAc (3 mL)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f1f6079ed67a43899f0dea34188da349
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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