Aluminium lithium hydride → N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

HRID 473086Notes

Reaction equation

HRID 473086 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]([S:10]([NH:13][CH:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23](OC)=[O:24])=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)(=[O:12])=[O:11])[CH3:9]>O1CCCC1>[OH:24][CH2:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[CH:14]([NH:13][S:10]([CH:8]([CH3:9])[CH3:7])(=[O:12])=[O:11])[CH2:15][CH2:16]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 67088221Methyl 1-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 67088175N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamideYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. Lithium Aluminium Hydride (2.102 mL, 5.04 mmol) was added dropwise to a stirred solution of methyl 1-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (1 g, 3.36 mmol) in Tetrahydrofuran (dry) (25 mL). Mixture warmed to rt and stirred for 4 hr. After this time the reaction mixture was again cooled to 0° C. and more Lithium Aluminium Hydride (2.102 mL, 5.04 mmol) added and the whole stirred at room temperature for 30 min before being carefully quenched with H2O (10 mL) and 2N NaOH (10 mL). The resulting mixture was filtered and partitioned between EtOAc and brine. The organic layer was separated, dried on Na2SO4 and solvent evaporated in vacuo to give a dark yellow oil Purification by flash chromatography (0-100% EtOAc in Heptane) afforded the title compound as a colourless oil (670 mg, 74%). MS (ESI): m/z [M−H]− 268.0

Workup

  1. customAt 0° C
  2. temperatureAfter this time the reaction mixture was again cooled to 0° C.
  3. stirringthe whole stirred at room temperature for 30 min
  4. custombefore being carefully quenched with H2O (10 mL) and 2N NaOH (10 mL)
  5. filtrationThe resulting mixture was filtered
  6. custompartitioned between EtOAc and brine
  7. customThe organic layer was separated
  8. customdried on Na2SO4 and solvent
  9. customevaporated in vacuo
  10. customto give
  11. customa dark yellow oil Purification by flash chromatography (0-100% EtOAc in Heptane)

Sources & evidence

ORD record
ord-7e7d5c8fe3dc4c2e9189460726857433
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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