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

HRID 742603Notes

Reaction equation

HRID 742603 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-f6825fe8ac8241d2bf9f400fd4643fd5
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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