Water → 2[6-[2-(N-Boc-Piperidin-4-yl)ethyl]-(3,4,5,6-tetrahydro-1,1-dioxo-2H-1,2-thiazin-2-yl)]acetaldehyde

HRID 2209454Notes

Reaction equation

HRID 2209454 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]2[S:21](=[O:23])(=[O:22])[N:20]([C:24](=[CH2:26])C)[CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C[O:30]CC1.O>C(OCC)(=O)C.O=[Os](=O)(=O)=O>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]2[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH:26]=[O:30])[CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 193809562-[6-[2-(N-Boc-Piperidin-4-yl)ethyl]-(3,4,5,6-tetrahydro-1,1-dioxo-2H-1,2-thiazin-2-yl)]prop-2-ene

Product 1

HCID 193809332[6-[2-(N-Boc-Piperidin-4-yl)ethyl]-(3,4,5,6-tetrahydro-1,1-dioxo-2H-1,2-thiazin-2-yl)]acetaldehyde

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 89 (0.50 g, 1.29 mmol), THF (16 mL), H2O (12 mL), and NaIO4 (0.69 g, 3.2 mmol) was added OsO4 (1 mL, 0.1 mmol; 2.5%/tert-butanol) to effect a white precipitate. After 3.0 h, the reaction mixture was diluted with ethyl acetate and washed with H2O, 5% KHSO4, sat. NaHCO3 and brine, dried (MgSO4), and concentrated to give aldehyde 90 as an oil.

Workup

  1. washwashed with H2O, 5% KHSO4, sat. NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6dd8d2e2e2484790ab8ffe5794905455
Source dataset
uspto-grants-1995_10
Patent number
US05455243

Reaction notes

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