With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.162021-14-9, name is (2-Amino-9H-fluoren-9-yl)methanol, molecular formula is C14H13NO, molecular weight is 211.26, as common compound, the synthetic route is as follows.HPLC of Formula: C14H13NO
Example 4 Synthesis of tert-Butyldimethylsiloxy-9-methyl-2-aminofluorene 5.91 g Imidazole (86.8 mmol, 2.1 equiv) was dissolved in 24 ml dry DMF and stirred 10 min in an iced bath under argon atmosphere. 7.47 g tertButyldimethylsilyl chloride (49.6 mmol, 1.2 equiv) dissolved in dry DMF was added. After 15 min stirring on ice 8.73 g 9-Hydroxymethyl-2-amino fluorene (41.3 mmol) dissolved in 40 ml dry DMF was added drop wise under cooling and argon atmosphere. The reaction was continued 15 min on ice and then at room temperature. The reaction was monitored by TLC [title product Rf=0.6, PE-MTBE (1:2)]. After 2 hours the starting product [Rf=0.1 PE-MTBE (1:2)] had disappeared and the reaction mixture was diluted with 400 ml CH2Cl2 and 100 ml 5% NaHCO3 was added. The organic phase was washed with 5*200 ml H2O and dried over Na2SO4. CH2Cl2 was eliminated by rotary evaporation and DMF was eliminated by azeotropic distillation with toluene. The residual brown oil (13.4 g, 99% yield) was analyzed by NMR and was used without further purification. 1H NMR (200 MHz/DMSO) delta=7.67-7.40 (3H; m; 3*Ar-H); 7.34-7.00 (2H; m; 2*Ar-H); 6.81 (1H; s; 1*Ar-H); 6.59 (1*; dd; J=8.02 Hz & 1.83 Hz; 1*Ar-H); 5.19 (2H; s; NH2); 3.97-3.76 (2H; m; CH2); 3.75-3.57 (1H; m; CH); 0.88 (9H; s; 3*CH3); 0.03 (6H; s; 2*CH3) 13C NMR (50 MHz/DMSO) delta=148.40 (Ar-Cqu); 145.81 (Ar-Cqu); 143.67 (Ar-Cqu); 141.88 (Ar-Cqu); 129.08 (Ar-Cqu); 127.10 (Ar-CH); 124.97 (Ar-CH); 124.16 (Ar-CH); 120.47 (Ar-CH); 117.87 (Ar-CH); 113.22 (Ar-CH); 110.58 (Ar-CH); 66.04 (CH2-OH); 49.60 (C9); 25.88 (3*CH3; t-Bu); 18.04 (Cqu; t-Bu), -5.04 (2CH3; Si-CH3)
At the same time, in my other blogs, there are other synthetic methods of this type of compound,162021-14-9, (2-Amino-9H-fluoren-9-yl)methanol, and friends who are interested can also refer to it.
Reference:
Patent; Baxter International Inc.; Baxter Healthcare SA; US2009/5574; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts