Hydrochloric Acid → (RS)-Toluene-4-sulfonic acid 5-methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-2-ylmethyl ester

HRID 278441Notes

Reaction equation

HRID 278441 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH2:12][OH:13])[CH2:6]2.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N([CH2:30][CH3:31])CC)C.Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21])[CH:7]([CH2:12][O:13][S:20]([C:17]1[CH:18]=[CH:19][C:30]([CH3:31])=[CH:15][CH:16]=1)(=[O:22])=[O:21])[CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22628355(RS)-(5-methoxy-2,3-dihydro-1H-indol-2-yl)-methanol

Product 1

HCID 86757886(RS)-Toluene-4-sulfonic acid 5-methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-2-ylmethyl esterYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(RS)-(5-methoxy-2,3-dihydro-1H-indol-2-yl)-methanol (100 mg, 0.46 mmol), p-toluenesulfonyl chloride (177 mg, 0.93 mmol), triethylamine (0.21 ml, 1.48 mmol) and N,N-dimethylamino pyridine (2 mg) were stirred for 18 hr at RT in CH2Cl2 (5 ml). 1N HCl (10 ml) was added, the mixture extracted with CH2Cl2 (2×25 ml) and the extracts washed with satd. NaCl solution (20 ml) and dried (Na2SO4). The crude material was chromatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-cyclohexane-Et3N (9:10:1) to afford the title compound as a yellow oil (172.8 mg, 0.35 mmol, 76%), MS: m/e=488.0 (M+H+).

Workup

  1. extractionthe mixture extracted with CH2Cl2 (2×25 ml)
  2. washthe extracts washed with satd
  3. dry with materialNaCl solution (20 ml) and dried (Na2SO4)
  4. customThe crude material was chromatographed over SiO2 (Merck 230-400 mesh)
  5. washeluting with EtOAc-cyclohexane-Et3N (9:10:1)

Sources & evidence

ORD record
ord-52b0b907ffca400bbd79314dd4b84bd8
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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