HCID 10988662, compound → Brucine

HRID 1033556Notes

Reaction equation

HRID 1033556 reaction equation
CN1C2C(=CC(OC)=CC=2)C(C)(CC(O)=O)C1=O.[CH3:19][O:20][C:21]1[CH:26]=[C:25]2[C@@:27]34[C@H:35]5[N:36]([C:37]([CH2:39][C@@H:40]6[O:41][CH2:42][CH:43]=[C:44]7[CH2:45][N:30]([C@H:31]3[CH2:32][C@@H:33]7[C@H:34]56)[CH2:29][CH2:28]4)=[O:38])[C:24]2=[CH:23][C:22]=1[O:46][CH3:47].O>O>[CH3:19][O:20][C:21]1[CH:26]=[C:25]2[C@@:27]34[C@@H:31]5[CH2:32][C@H:33]6[C:44]([CH2:45][N:30]5[CH2:29][CH2:28]3)=[CH:43][CH2:42][O:41][C@H:40]3[CH2:39][C:37](=[O:38])[N:36]([C@H:35]4[C@@H:34]63)[C:24]2=[CH:23][C:22]=1[O:46][CH3:47]

Participants

4

Reactant 2

HCID 10988662HCID 10988662, compoundHCID 16212366Brucine hydrate

Product 1

HCID 442021Brucine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acid 4 (7.1 g) and brucine hydrate (13.3 g) were dissolved in water (150 ml) under cautious warming. The clear solution was left standing for 12 h. at room temperature and the brucine salt filtered, and crystallized twice from water, to afford optically pure brucine salt of 5a (10.8 g): m.p. 115° degrees C.; [α]D-33.2 degrees (c=1.0, EtOH); C36H42N3O8 ·4 H2O: calc. C 60.34, H 6.98, N 5.87%; found C 60.59, H 6.81, N 5.87%. The brucine salt obtained above was dissolved in water (200 ml) under warming, 5N sodium hydroxide solution added (30 ml) and the brucine which precipitated removed by filtration. The brucine can be crystallized from acetone-water to afford material which is optically pure and can be reused. The filtrate was acidified with 2N hydrochloric acid and acid 5a extracted with ethylacetate, to afford after washing the extract with brine, drying (MgSO4) and concentration the optically pure acid 5a as colorless crystals (3.5 g) : m.p. 124°-125° degrees C.; [α] )D=-48.7° degrees (C.=0.96,CHCl3). The material is on TLC identical with racemic 4 (silica gel, CH2Cl2 with 1% MeOH).

Workup

  1. waitThe clear solution was left
  2. filtrationthe brucine salt filtered
  3. customcrystallized twice from water

Sources & evidence

ORD record
ord-fd387418aa884e1bb5999314258ea95d
Source dataset
uspto-grants-1994_05
Patent number
US05310935

Reaction notes

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