(-)-Anhydroecgonine methyl ester → 3beta-(3'-Methyl-4'-fluorophenyl)tropan-2beta-carboxylic acid methyl ester

HRID 1769253Notes

Reaction equation

HRID 1769253 reaction equation
[CH3:1][N:2]1[C@H:6]2[C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH2:9][C@@H:3]1[CH2:4][CH2:5]2.[CH3:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[CH:19][C:20]=1[F:21]>>[CH3:13][O:12][C:10]([C@H:7]1[C@@H:8]([C:17]2[CH:18]=[CH:19][C:20]([F:21])=[C:15]([CH3:14])[CH:16]=2)[CH2:9][C@H:3]2[N:2]([CH3:1])[C@@H:6]1[CH2:5][CH2:4]2)=[O:11]

Participants

3

Reactant 2

HCID 119478(-)-Anhydroecgonine methyl esterHCID 178427974HCID 178427974, compound

Product 1

HCID 103344673beta-(3'-Methyl-4'-fluorophenyl)tropan-2beta-carboxylic acid methyl esterYield 85.7%

Procedure

The title compound was prepared by modification of a reported procedure used to prepare other similar compounds.refThus, using anhydroecgonine methyl ester (500 mg, 2.76 mmol) and 3-methyl-4-fluorophenyl magnesium bromide (prepared from 200 mg of magnesium metal and 1 mL of 3-methyl-4-fluoro-1-bromobenzene) yielded 234 mg (29%) of the title compound. The hydrochloride salt had mp 163°-165° C.; [α]D25 -103.8° (c 0.08, MeOH); 1H NMR of free base of 41 (250 MHz, CDCl3) δ1.67 (m, 3), 2.15 (m, 2), 2.19 is, 3, CH3), 2.20 is, 3, NCH3), 2.55 (m, 2), 2.87 (m, 1, H-2), 2.93 (m, 1, H-3), 3.35 (m, 1, H-5), 3.49 (s, 3, OCH3), 3.55 (m, 1, H-1), 6.85, 6.97 (m, 3, C6H3).

Workup

  1. customThe title compound was prepared by modification of a reported procedure
  2. customto prepare other similar compounds.refThus

Sources & evidence

ORD record
ord-1219762831b249be82c99af09ba0513b
Source dataset
uspto-grants-1995_01
Patent number
US05380848

Reaction notes

Loading…