Sodium Bicarbonate → 3-(1-Phenylmethyl-2-pyrrolidinyl)phenol

HRID 233056Notes

Reaction equation

HRID 233056 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+]>Br>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 233612591-Phenylmethyl-2-(3-methoxyphenyl)pyrrolidine

Product 1

HCID 233612863-(1-Phenylmethyl-2-pyrrolidinyl)phenolYield 61%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1-Phenylmethyl-2-(3-methoxyphenyl)pyrrolidine in 48% hydrobromic acid (65 ml), was warmed to 110° C. for 2.5 hrs, and cooled to ambient temperature. The reaction mixture was neutralized with saturated sodium bicarbonate solution and extracted into 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, 1:1 ethyl acetate/dichloromethane). The appropriate fractions were collected and concentrated. The residue was flushed through alumina with ether to give 2.5 g (61%) of product, mp 113°-115° C.

Workup

  1. extractionextracted into 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, 1:1 ethyl acetate/dichloromethane)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated
  8. customThe residue was flushed through alumina with ether

Sources & evidence

ORD record
ord-d5ea806679fe46aa89ae70ae11e83630
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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