Methanol → HCID 86742753, compound

HRID 1382250Notes

Reaction equation

HRID 1382250 reaction equation
[I-].CN1C2C(=CC=CC=2)C([C@H]([C@H:14]2[NH:19][C:18](=[O:20])[C@@H:17]([CH2:21][CH2+:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]3[CH3:28])[NH:16][C:15]2=[O:29])C)=C1.CO.[BH4-].[Na+]>O>[CH3:28][N:23]1[CH:22]([CH2:21][CH:17]2[NH:16][C:15](=[O:29])[CH2:14][NH:19][C:18]2=[O:20])[CH:27]=[CH:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 887MethanolHCID 4311764Sodium borohydride

Product 1

HCID 86742753HCID 86742753, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of (3R,6R)-3-[(R)-1-(1-methylindol-3-yl)ethyl]-6-(1-methyl-2-pyridiniomethyl)piperazine-2,5-dione iodide (0.12 g), methanol (1.2 ml), and water (1.2 ml) was added sodium borohydride (0.12 g). The mixture was stirred on an ice bath for 1 hour, diluted with water (10 ml), and set aside in a refrigerator overnight. A precipitated solid was filtered, washed with water, and dried in vacuo to afford (3R,6R)-3-[(R)-1-methylindol-3-yl)ethyl]-6-[(RS)-1-methyl-1,2,3,6-tetrahydropyridin-6-yl-methyl]piperazine-2,5-dione (0.03 g).

Workup

  1. customset aside in a refrigerator overnight
  2. filtrationA precipitated solid was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9155efadf5f84ec1b2bc77c00fb6bb49
Source dataset
uspto-grants-1989_02
Patent number
US04806538

Reaction notes

Loading…