Ethylamine → HCID 57636333, compound

HRID 2110344Notes

Reaction equation

HRID 2110344 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([OH:31])[C@H:14]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)(=O)=O)=CC=1.[CH2:32]([NH2:34])[CH3:33]>CO>[F:30][C:26]1[CH:25]=[C:24]([C@H:14]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)[C@H:13]([OH:31])[CH2:12][NH:34][CH2:32][CH3:33])[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 86600896HCID 86600896, compound

Product 1

HCID 57636333HCID 57636333, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,3S)-3-(3-fluorophenyl)-2-hydroxy-3-(1H-indol-1-yl)propyl 4-methylbenzenesulfonate (200 mg, 0.456 mmol) was dissolved in a solution of ethylamine in methanol (2.0 M, 10 mL) and stirred for 12 hours in a sealed reaction vessel. All volatiles were removed under reduced pressure, and the liquid residue was dissolved in dichloromethane (15 mL), washed with a saturated aqueous solution of potassium carbonate, dried (anhydrous sodium sulfate), and concentrated. Purification of the liquid residue by Biotage chromatography (FlasH12i, silica, 0-15% MeOH/dichloromethane/0.5% triethylamine) gave (1S,2R)-1-(3-fluorophenyl)-1-(1H-indol-1-yl)-3-(ethylamino)propan-2-ol, which was used to prepare (1S,2R)-3-(ethylamino)-1-(3-fluorophenyl)-1-(1H-indol-1-yl)propan-2-ol hydrochloride as a white powder in an analogous matter to EXAMPLE 144, step 2. Yield: 99 mg (70%). MS (ES) m/z 313.1 ([M+H]+); HRMS: calcd for C19H21FN2O+H+, 313.1716; found (ESI, [M+H]+), 313.1716.

Workup

  1. customAll volatiles were removed under reduced pressure
  2. dissolutionthe liquid residue was dissolved in dichloromethane (15 mL)
  3. washwashed with a saturated aqueous solution of potassium carbonate
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customPurification of the liquid residue by Biotage chromatography (FlasH12i, silica, 0-15% MeOH/dichloromethane/0.5% triethylamine)

Sources & evidence

ORD record
ord-4784d50b24c14141af8fcc9caed15251
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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