B.O1[CH2:6][CH2:5][CH2:4]C1.[C:7]([NH:11][C:12](=O)[C:13]([CH2:16]C(C)C)([CH3:15])C)([CH3:10])([CH3:9])[CH3:8].Cl.[OH-].[Na+].O1CCC[CH2:25]1>O>[C:7]([N:11]([CH2:25][CH:5]([CH3:4])[CH3:6])[CH2:12][CH:13]([CH3:15])[CH3:16])([CH3:8])([CH3:9])[CH3:10]
Isobutyryl chloride (10.90 g, 0.1 mol) was added to a solution of tert-butylisobutylamine (25.85 g, 0.2 mol) in tetrahydrofuran (150 ml) at room temperature and stirred for 1 h. Solids were filtered off and washed with tetrahydrofuran ( 2×25 ml). N, N-tert-butylisobutyl-2-methylpropionamide was isolated by distillation to yield 18.50 g, (90%), bp 59-60° C./1.3 mm Hg. A 1 M borane-tetrahydrofuran solution (100 ml, 0,10 mol) was added dropwise to a solution of the amide (17.95 g, 90 mmol) in tetrahydrofuran (50 ml) at room temperature and the mixture refluxed for 1 h. Water (5 ml) was added after cooling, followed by a slow addition of 6 M hydrochloric acid (60 ml). Tetrahydrofuran was distilled off and solid sodium hydroxide (20.00 g, 0.5 mol) was added. The organic layer was separated and the aqueous solution was extracted with n-pentane (50 ml). The organic solutions were combined, dried over anhydrous magnesium sulfate, and the product was isolated by distillation to yield 14.24 g, (85%), bp 34-35° C./1.5 mm Hg; 1H NMR (CDCl3) δ0.84 (d, J=6.6 Hz, 12H, CH3), 1.01 (s, 9H, CH3), 1.58 (nonet, J=6.6 Hz, 2H, CH), 2.14 (d, J=6.6 Hz, 4H, CH2),
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