BOC-D-TRYPTOPHANOL

White solid

a) Compound 22; A solution of compound 1 (10.0 g, 33 mmol) and THF (50 mL) was cooled to 0 °C under Na) Compound 22; A solution of compound 1 (10.0 g, 33 mmol) and THF (50 mL) was cooled to 0 C under N2 atmosphere, then BH3/THF was added dropwise. The temperature of the reaction mixture was allowed warm to room temperature. After stirring for 16 hours, the reaction mixture was quenched by K2C03 (aq.), extracted with EtOAc (100 mL><3), the combined organic phase was washed with brine (50 mL) dried over Na2S04, concentrated in vacuo and purified with column (PE/EtOAc= 4: 1) to give the product 22 as white solid (5.72 g, 60 % yield). 1H NMR (400 MHz, CDC13): delta 1.46 (s, 9H), 3.02 (d, J= 6.8 Hz, 2H), 3.80-3.55 (m, 2H), 4.10-3.95 (m, 1H), 4.86 (br s, 1H), 7.07 (s, 1H), 7.16 (t, J = 7.2 Hz, 1H), 7.23 (t, J = 7.2 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H), 7.68 (d, J= 7.6 Hz, 1H), 8.20 (s, 1H).

Molecular Weight:290.36
XLogP3:2.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:290.16304257
Monoisotopic Mass:290.16304257
Topological Polar Surface Area:74.4
Heavy Atom Count:21
Complexity:354
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes