Aluminium lithium hydride → HCID 11551746, compound

HRID 2356987Notes

Reaction equation

HRID 2356987 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][N:22]=[C:23]=O)[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][NH:22][CH3:23])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58668699HCID 58668699, compound

Product 1

HCID 11551746HCID 11551746, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-(3-fluoro-benzenesulfonyl)-4-isocyanatomethyl-chroman (0.12 g, 0.35 mmol) in THF (15 ml) at 0° C. was added LiAlH4 (0.52 ml, 1.0 M in THF, 0.525 mmol). The mixture was stirred at 0° C. for 2 hours, then was quenched with one drop of H2O, 3 drops of 2N NaOH, and 3 drops of H2O again. The precipitate was filtered off. The solution was diluted with EtOAc, washed with water, dried with MgSO4, filtered and concentrated. The residue was purified with preparative TLC to give [7-(3-Fluoro-benzenesulfonyl)-chroman-4-ylmethyl]-methyl-amine free base, which was further treated with a few drops of 2N HCl in EtOH and dried under vacuum to give the corresponding HCl salt: 33.5 mg. MS: 336.2 (M+H)+, 377.2 (M+CH3CN+H)+, 671.3 (2M+H)+.

Workup

  1. customwas quenched with one drop of H2O, 3 drops of 2N NaOH, and 3 drops of H2O again
  2. filtrationThe precipitate was filtered off
  3. additionThe solution was diluted with EtOAc
  4. washwashed with water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with preparative TLC

Sources & evidence

ORD record
ord-1f0517df65124733ad08fc9a77756e55
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

Loading…