Iometopane → 2beta-Hydroxymethyl-3beta-(4-iodophenyl) tropane

HRID 1940450노트

반응식

HRID 1940450 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:14][C@H:13]3[N:15]([CH3:16])[C@H:10]([CH2:11][CH2:12]3)[C@H:9]2[C:17](OC)=[O:18])=[CH:4][CH:3]=1.[BH4-].[Li+]>C(OCC)C>[OH:18][CH2:17][C@H:9]1[C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)[CH2:14][C@H:13]2[N:15]([CH3:16])[C@@H:10]1[CH2:11][CH2:12]2

참가 물질

4

반응물 2

HCID 108220IometopaneHCID 4148881Lithium borohydride

생성물 1

HCID 695463482beta-Hydroxymethyl-3beta-(4-iodophenyl) tropane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  1. customThe reaction is quenched with water
  2. extractionthe aqueous phase of the mixture is extracted with methylene chloride
  3. customThe organic phase is collected
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is removed

출처 및 근거

ORD 기록
ord-575d060d149a4f31b7ace80d061c6837
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700446

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