Ethylamine → HCID 68904340, compound

HRID 2110329Notes

Reaction equation

HRID 2110329 reaction equation
[ClH:1].Cl.[N:3]1([CH:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:13]([OH:22])[CH2:14][N:15]2CCN(C)[CH2:17][CH2:16]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.C(N)C>>[ClH:1].[CH2:16]([NH:15][CH2:14][CH:13]([OH:22])[CH:12]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:17]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 68906810HCID 68906810, compound

Product 1

HCID 68904340HCID 68904340, compound

Procedure

In an analogous manner to EXAMPLE 1, step 3, a solution of (2RS,3RS)-toluene-4-sulfonic acid 2-hydroxy-3-indol-1-yl-3-phenyl-propyl ester (EXAMPLE 1, step 3, 0.42 g, 1.0 mmol) and ethylamine (2 N solution in methanol, 5 mL) was stirred in a sealed flask at room temperature for 15 hours. After dilution with a saturated aqueous solution of sodium bicarbonate, the mixture was extracted with a solution of dichloromethane/isopropyl alcohol (3/1). The extract was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on via Biotage chromatography (FlasH40i, silica, dichloromethane, 5% methanol/dichloromethane) to give an oil as free base of the expected product. The free base was dissolved in a minimum amount of ethanol and treated with a 1 N ethereal solution of hydrochloric acid until the solution was pH=3 followed by diethyl ether. The product was then crystallized by adding a minimum amount ethyl acetate to afford the titled compound, (1RS,2SR)-3-(ethylamino)-1-(1H-indol-1-yl)-1-phenylpropan-2-ol hydrochloride as a tan solid. MS (ES) m/z 295.2 ([M+H]+); HRMS: calcd for C19H22N20+H+, 295.18049; found (ESI, [M+H]+), 295.1797.

Workup

  1. extractionAfter dilution with a saturated aqueous solution of sodium bicarbonate, the mixture was extracted with a solution of dichloromethane/isopropyl alcohol (3/1)
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified on via Biotage chromatography (FlasH40i, silica, dichloromethane, 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-d9adff015f9544b8adc29785e75a91d1
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

Loading…