D-Tartaric acid → 2beta-hydroxymethyl-3beta-(4-iodophenyl)-tropane-D-Tartrate

HRID 1940451Notes

Reaction equation

HRID 1940451 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH2:8][C@H:7]2[N:17]([CH3:18])[C@@H:4]1[CH2:5][CH2:6]2.[C:19]([OH:28])(=[O:27])[C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21]>CO>[C:24]([C@H:22]([C@@H:20]([C:19]([OH:28])=[O:27])[OH:21])[OH:23])([OH:26])=[O:25].[OH:1][CH2:2][C@H:3]1[C@@H:9]([C:10]2[CH:11]=[CH:12][C:13]([I:16])=[CH:14][CH:15]=2)[CH2:8][C@H:7]2[N:17]([CH3:18])[C@@H:4]1[CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 695463482beta-Hydroxymethyl-3beta-(4-iodophenyl) tropane

Product 1

HCID 867517502beta-hydroxymethyl-3beta-(4-iodophenyl)-tropane-D-Tartrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As shown in FIG. 1, 5 mmol 3β-(4-iodophenyl)-2β-(carbomethoxy)tropane (β-CIT (1)) is dissolved in 25 ml ethyl ether at 0° C., and 2 equivalents of lithium borohydride (LiBH4) are added. The temperature is raised to room temperature, and stirring is continued for approximately 2 hr. The reaction is quenched with water and the aqueous phase of the mixture is extracted with methylene chloride. The organic phase is collected and dried over magnesium sulfate and the solvent is removed to give 2β-hydroxymethyl-3β-(4-iodophenyl) tropane free base (2) in quantitative yield. 2β-hydroxymethyl-3β-(4-iodophenyl)tropane was fully characterized as D-tartaric acid: mp=90°-92° C., [α]D20 -66.3° C. (c, 0.525, MeOH). 1H NMR (250 MHz, CDCl3): δ 7.59 (d, J=8.4 Hz, 2H); 6.99 (d, J=8.4 Hz, 2H); 3.76 (dd, J=11.06 Hz; 1H); 3.44 (d, J=4.59 Hz, 1H); 3.32 (m, 2H); 3.01 (m, 1H); 2.47 (td; J=2.88 Hz, J=12.74 Hz; 1H); 2.20 (s, 3H); 2.16 (m, 2H); 1.70 (m, 2H); 1.65 (m, 1H), 1.46 (m, 1H). Anal. (C15H20 NO1) (C4H6O6): CHN.

Sources & evidence

ORD record
ord-a2495b052c014131971f7cd12b0a6843
Source dataset
uspto-grants-1997_12
Patent number
US05700446

Reaction notes

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