6-((tert-butyldimethylsilyl)oxy)hexan-1-amine synthesis
- Product Name:6-((tert-butyldimethylsilyl)oxy)hexan-1-amine
- CAS Number:124883-99-4
- Molecular formula:C12H29NOSi
- Molecular Weight:231.45
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Yield:124883-99-4 99.3%
Reaction Conditions:
with dmap;triethylamine in dichloromethane at 0 - 20; for 18 h;
Steps:
Step-1: Synthesis of compound 3
To a solution of 6-aminohexanol (1) (1 eq.) in DCM (500 mL) was added DMAP (0.1 eq.) at ambient temperature and reaction mixture was cooled to 0 °C. Triethyl amine (1.5 eq.) and tert-butyldimethylsilyl chloride (1.2 eq) were added sequentially. Reaction mixture was allowed to come to ambient temperature and stirred at same temperature for 18 h. TLC (10 % methanol in DCM, stain visualization-ninhydrin) showed that starting material was consumed. After completion, reaction mixture was concentrated under vacuum and suspension was filtered off. Filterate was concentrated under reduced pressure to afford 6-((tert-butyldimethylsilyl)oxy)hexan-1-amine (3). Yield: 99.3 %; colourless oil which was used as such for further reactions LC-MS (ESI) m/z calculated for C16H30N30SiCl (M + H)+: 231.20. 1HNMR (400 MHz, chloroform-d1): δ 5.80-5.60 (s, b, 2H), 3.60 (s, 2H), 2.83-2.88 (m, 2H), 1.66 (m, 2H), 1.28-1.54 (m, 6H), 0.83 (br, s, 9H), 0.00 (s, 6 H); 13C NMR (101 MHz, DMSO-d6): δ 63.0, 41.5, 32.7, 32.5, 25.9, 25.9, 25.5, 18.2, 18.2, 18.2, 5.4, 5.4; Anal. calcd. (%) for C12H29NOSi: C, 62.27; H, 12.63; N, 6.05; found (%): C, 62.39; H, 12.56; N, 6.07.
References:
Sharma, Vijay Kumar;Barde, Anup;Rattan, Sunita [Asian Journal of Chemistry,2020,vol. 32,# 5,p. 1101 - 1108]
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