HCID 68486860, compound → HCID 25019922, compound

HRID 1259452Notes

Reaction equation

HRID 1259452 reaction equation
O.[OH:2][CH2:3][C@@H:4]1[O:17][C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5]1)[NH:12][C:11](=[O:16])[CH2:10]3>N1C=CC=CC=1>[OH:2][CH2:3][C@@H:4]1[O:17][C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5]1)[NH:12][C:11](=[O:16])[CH2:10]3

Participants

3

Reactant 1

HCID 68486860HCID 68486860, compound

Product 1

HCID 25019922HCID 25019922, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 200 mL flask is charged with (2S)-2-(hydroxymethyl)-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one hydrate (9.37 g, 39.2 mmol) and pyridine (60 mL). The pyridine is removed by rotary evaporation to give (2S)-2-(hydroxymethyl)-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one as a brown paste. The residue is dissolved in fresh pyridine (60 mL), the solution is heated to 30° C., and p-toluenesulfonyl chloride (11.20 g, 58.8 mmol) in toluene (23.5 mL) is added over 30 min. The solution is stirred for 8 h, and then isopropanol (100 mL) is added. The resulting suspension is cooled to 5° C. and the precipitate is collected by vacuum filtration. The filter cake is washed with isopropanol (20 mL) and suction dried to give the title compound (7.81 g, 53%) as a yellow powder. LCMS (Standard Method): 2.50 min, 376 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 10.19 (br s, 1H), 7.76 (d, J=8.1 Hz, 2H), 7.41 (d, J=8.1 Hz, 2H), 6.63 (d, J=8.2 Hz, 1H), 6.27 (d, J=8.2 Hz, H), 4.51-4.46 (m, 1H), 4.32 (dd, J=3.0, 11.3 Hz, 1H), 4.20-4.14 (m, 2H), 3.96 (dd, J=5.9, 11.6 Hz, 1H), 3.13 (ABq, 2H, J=22.3 Hz, Δv=42.4 Hz), 2.38 (s, 3H).

Workup

  1. customThe pyridine is removed by rotary evaporation

Sources & evidence

ORD record
ord-3cf6f1e1b65f4ecbb7bfc95be2f69f95
Source dataset
uspto-grants-2013_06
Patent number
US08466296B2

Reaction notes

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