Sodium Sulfite → HCID 67440013, compound

HRID 1664785Notes

Reaction equation

HRID 1664785 reaction equation
[CH3:1][O:2][C:3]([CH:5]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:17][CH2:16]1)[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=C)=[O:4].I([O-])(=O)(=O)=[O:32].[Na+].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]([CH:5]([CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:19][CH2:20]1)[CH2:6][C:7](=[O:32])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:4]

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 67440613HCID 67440613, compound

Product 1

HCID 67440013HCID 67440013, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Osmium tetroxide (2.5 wt. % in t-BuOH; 0.2 mL, 0.001 mmol) was added to a solution of benzyl 4-[1-(methoxycarbonyl)-3-phenylbut-3-en-1-yl]piperidine-1-carboxylate (2.11 g, 5.19 mmol) in tetrahydrofuran (20 mL). Sodium periodate (3.33 g, 15.6 mmol) in water (17 mL) was added to the reaction mixture. After 18 h, saturated aqueous sodium sulfite and saturated aqueous sodium bicarbonate were added and the mixture was extracted with ethyl acetate (4×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to give the title compound. MS 410.1 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4×)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5dd042ebae244b6b8e3722763f53f9fd
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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