Triethylamine → HCID 66643231, compound

HRID 536707Notes

Reaction equation

HRID 536707 reaction equation
COC1C=CC(C(C2C=CC(OC)=CC=2)(C2C=CC=CC=2)[O:10][CH2:11][C@@H:12]2[C@@H:16]([O:17][CH3:18])[CH2:15][CH2:14][O:13]2)=CC=1.O.CC1C=CC(S(O)(=O)=O)=CC=1.CCN(CC)CC>C(Cl)Cl.CO>[CH3:18][O:17][C@H:16]1[CH2:15][CH2:14][O:13][C@@H:12]1[CH2:11][OH:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 66646915HCID 66646915, compound

Product 1

HCID 66643231HCID 66643231, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Example 22D (2.6 g, 6 mmol) in CH2Cl2 (10 mL) and MeOH (10 mL) was treated with 4-methylbenzenesulfonic acid monohydrate (570 mg, 3 mmol). The mixture was stirred at rt for 1 hr. The mixture was neutralized with excess Et3N. The solvent was removed and the residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% MeOH in ethyl acetate) to afford 580 mg (73%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.85 (t, J=6.14 Hz, 1H) 1.95-2.03 (m, 2H) 3.35 (s, 3H) 3.56-3.65 (m, 1H) 3.71-3.78 (m, 1H) 3.82 (dd, J=8.29, 4.30 Hz, 1H) 3.85-3.93 (m, 2H) 3.95-4.02 (m, 1H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7f9e285991ee49b3ad600246b6e48014
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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