Methanol → HCID 22033130, compound

HRID 1859326Notes

Reaction equation

HRID 1859326 reaction equation
[OH:1][C:2]1[CH:37]=[CH:36][C:5]2[CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:7]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)([CH3:10])[CH2:8][O:9][C:4]=2[CH:3]=1.C[OH:39]>O>[OH:1][C:2]1[CH:37]=[CH:36][C:5]2[CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27]([CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:39])[C:7]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)([CH3:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 22123604HCID 22123604, compound

Product 1

HCID 22033130HCID 22033130, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(3RS,4RS)-7-Hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(2-piperidinoethylthio)nonyl]-2,3-dihydro-4H-benzopyran (126 mg, 0.24 mmol) was dissolved in methanol (5 ml)and water (1.2 ml), and NaIO4 (62 mg, 0.29 mmol) was added thereto. The reaction was stirred for 4 hours at room temperature and then filtered. The filtrate was concentrated and the residue was purified with flash column chromatography (dichloromethane:ethanol=13:1→10:1) to obtain 96 mg (yield: 74%) of the title compound as a white foamy solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified with flash column chromatography (dichloromethane:ethanol=13:1→10:1)

Sources & evidence

ORD record
ord-7c54fa1c019c4355a0be8308bc33d038
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

Loading…