tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At −60° C., a solution of DMSO (1.73 ml, 24.4 mmol) in CH2Cl2 (20 mL) was added dropwise to a 2M solution of oxalyl chloride (1.28 mL, 14.7 mmol) in CH2Cl2 (7 mL). The mixture was stirred for 20 minutes and then a solution of tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate (2.8 g, 12.2 mmol) in CH2Cl2 (7 mL) was added dropwise. The mixture was stirred for 10 minutes and triethylamine (8.51 ml, 61.1 mmol) was slowly added. The reaction mixture was warmed to ambient temperature and water was added. When the mixture became clear, it was extracted with CH2Cl2, the solvent evaporated to afford crude tert-butyl 4-formylazepane-1-carboxylate (2.78 g, 100%). The mixture was stirred for 10 minutes it was extracted with CH2Cl2 the solvent evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-tert-Butyl 4-ethyl azepane-1,4-dicarboxylate (3.3 g, 12 mmol, US Publication No. 2006/229289) was dissolved in THF (100 mL) and cooled in an ice bath. LiAlH4 (12 mL, 12 mmol) was added slowly and stirred for 30 minutes. Water (˜3 mL) was added slowly, followed by Na2SO4. The reaction was filtered and concentrated to afford crude tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate (2.8 g, 100%). cooled in an ice bath The reaction was filtered concentrated