Chloroform → (2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate

HRID 859999Notes

Reaction equation

HRID 859999 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14][C@H:13]([CH2:16][OH:17])[O:12][C:8]3=2)[N:3]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].C(N(CC)CC)C.C(Cl)(Cl)Cl>C(Cl)Cl.O>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:17][CH2:16][C@@H:13]2[O:12][C:8]3=[C:9]4[C:4](=[CH:5][CH:6]=[C:7]3[O:15][CH2:14]2)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]4)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11183845[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol

Product 1

HCID 11280604(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonateYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol (0.13 g, 0.57 mmol), tosyl chloride (0.16 g, 0.82 mmol) and triethylamine (0.65 mL, 4.7 mmol) in CH2Cl2 (8 mL) was stirred at room temperature for 18 hours. CHCl3 (30 mL) and H2O (30 mL) were added. The two layers were separated. The aqueous layer was extracted with CHCl3 (20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification on SiO2, eluting with (1:1) hexane:EtOAc gave 0.19 g (88%) of the title compound as a brown syrup: mp 115–117° C.; 1H NMR (CDCl3) δ 8.12 (d, J=8.6 Hz, 1H), 7.76 (m, 2H), 7.51 (d, J=9 Hz, 1H), 7.20–7.60 (m, 4H), 4.5–4.6 (m, 1H), 4.2–4.4 (m, 3H), 4.1–4.2 (m, 1H), 2.70 (s, 3H), 2.39 (s, 3H);

Workup

  1. customThe two layers were separated
  2. extractionThe aqueous layer was extracted with CHCl3 (20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification on SiO2
  7. washeluting with (1:1) hexane

Sources & evidence

ORD record
ord-313ef3453d184bb8ae8515a424751035
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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