Aluminium lithium hydride → HCID 59497801, compound

HRID 1011511Notes

Reaction equation

HRID 1011511 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@H:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[C:23](OCC)=[O:24])(=[O:16])=[O:15])=[CH:10][CH:9]=1>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@@H:18]2[CH2:22][CH2:21][CH2:20][C@@H:19]2[CH2:23][OH:24])(=[O:15])=[O:16])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90811846cis-Ethyl 2-(4-chlorophenylsulfonamido)cyclopentanecarboxylate

Product 1

HCID 59497801HCID 59497801, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (9.36 mL, 9.36 mmol) was added dropwise to a solution of cis-ethyl 2-(4-chlorophenylsulfonamido)cyclopentanecarboxylate (2.07 g, 6.24 mmol) in 40 mL anhydrous tetrahydrofuran under nitrogen at 0° C. The reaction was then stirred for 1 h at room temperature, then quenched by the slow addition of 100 mL ethyl acetate. The reaction was partitioned between 600 mL ethyl acetate and 300 mL saturated ammonium chloride. The organic layer was dried on sodium sulfate and concentrated to yield 4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (1.81 g, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77-7.85 (2H, m), 7.45-7.50 (2H, m), 5.38 (1H, d, J=7.05 Hz), 3.61-3.78 (3H, m), 2.04-2.15 (1H, m), 1.27-1.80 (7H, m). LC/MS R.T.=2.46 min; [M+H]+=290.10.

Workup

  1. customquenched by the slow addition of 100 mL ethyl acetate
  2. customThe reaction was partitioned between 600 mL ethyl acetate and 300 mL saturated ammonium chloride
  3. customThe organic layer was dried on sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4840887b7fa34988ad7c16830b6ae509
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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