11-((tert-Butoxycarbonyl)amino)undecanoic acid → N-Boc-11-aminoundecan-1-ol

Temperature

0 °C

Compound 1 (29.0 g, 96.2 mmol) was dissolved in anhydrous tetrahydrofuran (500 mL). The solution was cooled to 0° C. under a dry inert atmosphere. Borane-tetrahydrofuran complex (1.0 M, 144 mL, 144 mmol) was added dropwise with stirring over 1 hour. The cooling bath was removed and the reaction was allowed to warm to room temperature and stirred an additional 2 hours. The reaction was then quenched by the slow, careful addition of saturated aqueous sodium bicarbonate solution (100 mL). The mixture was diluted with water (400 mL), and the tetrahydrofuran was removed in vacuo. The resulting mixture was extracted three times with ethyl acetate (200 mL portions), and the organic extracts were combined. The ethyl acetate solution was washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo. A white waxy solid was obtained (27.1 g, 98% yield), which was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6): δ 1.23 (m, 14H), 1.30–1.43 (m, 13H), 2.88 (q, J=6.7 Hz, 2H), 3.36 (q, J=6.3 Hz, 2H), 4.31 (t, J=5.1 Hz, 1H), 6.74 (t, J=5.2 Hz, 1H). 13C NMR (75 MHz, DMSO-d6): δ 25.13, 26.27, 28.25, 28.74, 28.98, 29.03, 29.11, 29.48, 32.56, 60.72, 77.21, 155.55. HRMS (ESI-pos): calcd for C16H34NO3 288.2539, obsd 288.2535.

1. additionBorane-tetrahydrofuran complex (1.0 M, 144 mL, 144 mmol) was added dropwise
2. customThe cooling bath was removed
3. temperatureto warm to room temperature
4. stirringstirred an additional 2 hours
5. customThe reaction was then quenched by the slow,
6. additioncareful addition of saturated aqueous sodium bicarbonate solution (100 mL)
7. additionThe mixture was diluted with water (400 mL)
8. customthe tetrahydrofuran was removed in vacuo
9. extractionThe resulting mixture was extracted three times with ethyl acetate (200 mL portions)
10. washThe ethyl acetate solution was washed with brine (100 mL)
11. dry with materialdried over anhydrous magnesium sulfate
12. filtrationfiltered
13. customevaporated in vacuo
14. customA white waxy solid was obtained (27.1 g, 98% yield), which
15. customwas used in the next step without further purification

ORD record

ord-4ae1b3b5d2f245a5a588e7ce0a0b0dcb

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208322B2