Water → HCID 19428302, compound

HRID 1078766Notes

Reaction equation

HRID 1078766 reaction equation
C(O[C:4]([CH:6]1[O:48][C:9]2[CH:10]=[C:11]3[C:16](=[C:17](C(OCC)=O)[C:8]=2[O:7]1)[CH2:15][N:14]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([O:46][CH3:47])[CH:39]=1)[S:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1)[CH2:13][CH2:12]3)=[O:5])C.[BH4-].[Li+].O.[O:52]1CCC[CH2:53]1>>[CH3:47][O:46][C:40]1[CH:39]=[C:38]([CH:29]([S:30][C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][N:14]2[CH2:13][CH2:12][C:11]3[CH:10]=[C:9]4[O:48][C:6]([CH2:4][OH:5])([CH2:53][OH:52])[O:7][C:8]4=[CH:17][C:16]=3[CH2:15]2)[CH:43]=[CH:42][C:41]=1[O:44][CH3:45]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 86749758HCID 86749758, compound

Product 1

HCID 19428302HCID 19428302, compound

Procedure

A mixture of 0.31 g of diethyl-6-[7-(3,4-dimethoxyphenyl)-7-[(4-methylphenyl)thio]heptyl]-5,6,7,8-tetrahydro-1,3-dioxolo [4,5-g]isoquinoline dicarboxylate and 0.045 g of lithium borohydride in 20 mL of tetrahydrofuran is stirred at room temperature for 3 hours, poured into water and the solvent evaporated in vacuo. The resulting mixture is extracted with methylene chloride. The methylene chloride extract is dried, filtered and the filtrate is evaporated in vacuo to yield a yellow oil. This oil is purified by flash chromatography using 2% methyl alcohol in methylene chloride to yield 0.1 g of the desired product as a white foam.

Workup

  1. customthe solvent evaporated in vacuo
  2. extractionThe resulting mixture is extracted with methylene chloride
  3. extractionThe methylene chloride extract
  4. customis dried
  5. filtrationfiltered
  6. customthe filtrate is evaporated in vacuo
  7. customto yield a yellow oil
  8. customThis oil is purified by flash chromatography

Sources & evidence

ORD record
ord-45523c933f814b8195e112e3de42db72
Source dataset
uspto-grants-1996_08
Patent number
US05550149

Reaction notes

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