Hydrogen Bromide → HCID 23361275, compound

HRID 1654043Notes

Reaction equation

HRID 1654043 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:7][CH:8]=1.Br.C(=O)(O)[O-].[Na+]>>[C:16]1([CH2:15][CH2:14][N:10]2[CH2:11][CH2:12][CH2:13][CH:9]2[C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 23361279HCID 23361279, compound

Product 1

HCID 23361275HCID 23361275, compoundYield 96%

Procedure

2-(3-Methoxyphenyl)-1-(2-phenylethyl)pyrrolidine and 48% hydrobromic acid (15 ml) were warmed to 105° C. for 3.5 hrs and cooled to ambient temperature. The reaction mixture was neutralized with saturated sodium bicarbonate solution, and the mixture was extracted with dichloromethane (2 times). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, ether). The appropriate fractions were collected and concentrated to afford 1.1 g (96%) of 3-[1-(2-phenylethyl)-2-pyrrolidinyl]phenol.

Workup

  1. extractionthe mixture was extracted with dichloromethane (2 times)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, ether)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-912e406c56d44310be645942ef77d2b6
Source dataset
uspto-grants-1995_04
Patent number
US05405845

Reaction notes

Loading…