Triacetoxyperiodinane → HCID 86660507, compound

HRID 1506588Notes

Reaction equation

HRID 1506588 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[OH:23][CH:24]([C:33]1[N:34]=[C:35]([CH:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]2)[S:36][CH:37]=1)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[C:27]1([CH2:26][CH2:25][C:24]([C:33]2[N:34]=[C:35]([CH:38]3[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]3)[S:36][CH:37]=2)=[O:23])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67468382HCID 67468382, compound

Product 1

HCID 86660507HCID 86660507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (15% strength solution in dichloromethane, 8.3 g) was added dropwise to a solution of tert-butyl 4-[4-(1-hydroxy-3-phenylpropyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (790 mg) in dichloromethane (7.9 ml). The reaction mixture was stirred at room temperature overnight. 5 g of silica gel were then added, and the solvent was removed under reduced pressure. The residue was purified chromatographically. This gave tert-butyl 4-[4-(3-phenylpropanoyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (545 mg).

Workup

  1. addition5 g of silica gel were then added
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-50ce7e8adb0740a3891729826f18008f
Source dataset
uspto-grants-2015_12
Patent number
US09220266B2

Reaction notes

Loading…