Aluminium lithium hydride → HCID 59497810, compound

HRID 1011539Notes

Reaction equation

HRID 1011539 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[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[C:25](OC)=[O:26])(=[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[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[CH2:25][OH:26])(=[O:15])=[O:16])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66669620trans-Methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate

Product 1

HCID 59497810HCID 59497810, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (1.10 mL, 1.10 mmol) was added dropwise to a solution of trans-methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate (253 mg, 0.73 mmol) in anhydrous tetrahydrofuran at −60° C. under nitrogen. The reaction was stirred at room temperature for 1.5 h and quenched by the addition of 25 mL ethyl acetate. The reaction was extracted twice with 25 mL saturated aqueous ammonium chloride. The organic layer was dried over sodium sulfate and concentrated to yield 4-chloro-N-(trans-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (216 mg, 93%). 1H NMR (400 MHz, CDCl3) δ ppm 7.81-7.83 (1H, m), 7.79-7.80 (1H, m), 7.47-7.49 (1H, m), 7.44-7.46 (1H, m), 5.40 (1H, d, J=8.06 Hz), 3.64 (1H, dd, J=11.08, 4.78 Hz), 3.48 (1H, dd, J=10.95, 4.41 Hz), 3.15-3.27 (1H, m), 2.27 (1H, br. s.), 1.58-1.72 (2H, m), 1.42-1.55 (5H, m), 1.21-1.39 (4H, m). LC/MS R.T.=2.18 min; [M+H]+=318.08; [M+Na]+=340.09; [M−H]−=316.07.

Workup

  1. customquenched by the addition of 25 mL ethyl acetate
  2. extractionThe reaction was extracted twice with 25 mL saturated aqueous ammonium chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69375b2e46f44a8bafc602832341b9b6
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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