Triethylamine → 4-{[(2,3-dihydro-1H-inden-2-ylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

HRID 1798421Notes

Reaction equation

HRID 1798421 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.S=C1N([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29](=[O:31])[CH3:30])=[C:24]([O:32][CH3:33])[CH:23]=2)=[O:19])CCS1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[C:29]([O:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:18](=[O:19])[NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4]2)=[CH:23][C:24]=1[O:32][CH3:33])(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1227642-Aminoindan hydrochlorideHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 568479154-{[(2,3-dihydro-1H-inden-2-ylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetateYield 42.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Aminoindane hydrochloride (166 mg, 1.1×0.891 mmol) was suspended in solution of VII (304.2 mg, 0.891 mmol) in anhydrous THF (10 mL), triethylamine (198 mg, 275 μL, 2.2×0.891 mmol) was added dropwise, and the reaction mixture was stirred at room temperature for 1 hour. The mixture was diluted with CH2Cl2 and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (1:1, v/v) to afford 134 mg (42%) white solid, 14: mp=114-116° C. (uncorrected); Rf=0.45 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 7.20 (bs, 2H), 7.15 (m, 2H), 6.98 (d, 3J=8.0 Hz, 1H), 6.93 (d, 1H), 6.90 (dd, 3J=8.0 Hz, 1H), 5.04 (s, 2H, CH2O), 4.51 (bs, 2H), 3.81 (s, 3H, OCH3), 3.28 (dd, 3J=16 Hz, 4J=7.1 Hz, 2H), 2.80 (dd, 3J=16 Hz, 4J=4.5 Hz, 2H, NCH2), and 2.29 (s, 3H). Exact mass (ESI) calculated for C20H22NO5 [M+H]=356.1492. found 356.1496.

Workup

  1. additionwas added dropwise
  2. washwashed with 1N HCl
  3. distillationdistilled water, and saturated NaCl
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5da322b4cf7e4d69804348482ebb35ed
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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