Diisobutylaluminumhydride → HCID 89533741, compound

HRID 920224Notes

Reaction equation

HRID 920224 reaction equation
[CH3:1][S:2]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:15](OC)=[O:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)(=[O:4])=[O:3].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH3:1][S:2]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][OH:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 89526098HCID 89526098, compound

Product 1

HCID 89533741HCID 89533741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The compound of Formula 8-2 (0.080 g, 0.297 mmol) was dissolved in 1.5 mL of THF and the solution was cooled to 0° C., then treated with 1.5 mL di-isobutyl aluminum hydride (DIBAl—H 1.5 mmol). The reaction mixture was stirred for 1 hour maintaining the temperature at 0° C., then quenched with 2N HCl and stirred at RT for 30 minutes additional. The reaction mixture was extracted into EtOAc three times. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to yield 8-3 ([2-(methylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-8-yl]methanol).

Workup

  1. temperaturemaintaining the temperature at 0° C.
  2. customquenched with 2N HCl
  3. stirringstirred at RT for 30 minutes additional
  4. extractionThe reaction mixture was extracted into EtOAc three times
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee5e47b992ef465c931dc9139c5a9536
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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