Aluminium lithium hydride → 4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide
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]=1Participants
Conditions
- Temperature
- -60 °C
Procedure
A 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (7.5 mL, 7.5 mmol) was added dropwise to a solution of cis-methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate (1.73 g, 5.0 mmol) in 60 mL anhydrous tetrahydrofuran under nitrogen cooled to −60° C. The reaction was stirred for 1.5 h at room temperature and quenched by the slow addition of 150 mL ethyl acetate followed by 150 mL saturated aqueous ammonium chloride. The layers were separated and the aqueous layer was extracted an additional two times with 150 mL ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to yield 4-chloro-N-(cis-2-(hydroxymethyl)cycloheptyl)benzenesulfonamide (1.55 g, 98%). 1H NMR (400 MHz, CDCl3) δ ppm 7.82-7.84 (1H, m), 7.80-7.82 (1H, m), 7.48-7.50 (1H, m), 7.45-7.47 (1H, m), 5.13 (1H, d, J=9.57 Hz), 3.70-3.80 (1H, m), 3.61 (1H, dd, J=11.21, 10.20 Hz), 3.41 (1H, dd, J=11.46, 4.66 Hz), 2.69 (1H, br. s.), 1.67-1.83 (1H, m), 1.53-1.62 (2H, m), 1.26-1.51 (7H, m), 1.05-1.20 (1H, m).
Workup
- customquenched by the slow addition of 150 mL ethyl acetate
- customThe layers were separated
- extractionthe aqueous layer was extracted an additional two times with 150 mL ethyl acetate
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d68c9da0dca14c37af11582e7a0f2b5c
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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