Aluminium lithium hydride → HCID 58724177, compound

HRID 2356222Notes

Reaction equation

HRID 2356222 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][CH2:19]C2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][CH2:19]2)[CH2:13][CH2:12]1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58724166HCID 58724166, compound

Product 1

HCID 58724177HCID 58724177, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 1-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)cyclobutanecarboxylate (47 mg, 0.13 mmol) was dissolved in THF (3 ml). Lithium aluminum hydride (0.32 ml, 1.0 M in THF) was added at 0° C. The reaction mixture was stirred at 0° C. for 45 minutes. It was quenched by careful addition of EtOAc at 0° C. The mixture was stirred for another 30 minutes before 1N NaOH and equal volume of brine were added. The mixture was extracted with EtOAc three times. Combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography (SiO2, 70% EtOAc/hexanes) to give the title compound (20 mg, 8% 3 steps) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm: 0.51-0.54 (m, 2 H), 0.60-0.63 (m, 2 H), 1.74 (bs, 1 H), 2.80-2.84 (m, 4 H), 3.17-3.24 (m, 4 H), 3.56 (s, 2 H), 7.38 (td, J=7.4, 1.6 Hz, 1 H), 7.45-7.52 (m, 2 H), 8.00 (dd, J=7.7, 1.6 Hz, 1 H); 13C NMR (100 MHz, CHLOROFORM-D) δ ppm 12.2, 46.5, 46.6, 49.7, 64.7, 127.0, 132.1, 132.3, 132.4, 133.6, 135.9; ESI-MS: m/z 331.2 (M+H)+.

Workup

  1. customIt was quenched by careful addition of EtOAc at 0° C
  2. stirringThe mixture was stirred for another 30 minutes before 1N NaOH and equal volume of brine
  3. additionwere added
  4. extractionThe mixture was extracted with EtOAc three times
  5. dry with materialCombined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (SiO2, 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b31cde930f404be293fd75d5d7301d27
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

Loading…