Triacetoxyperiodinane → HCID 90419000, compound

HRID 514871Notes

Reaction equation

HRID 514871 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([O:19][CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH2:14][CH:15]([CH3:18])[CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([O:19][CH2:20][O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([CH2:14][CH:15]([CH3:18])[CH:16]=[O:17])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 90419029HCID 90419029, compound

Product 1

HCID 90419000HCID 90419000, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-4-((benzyloxy)methoxy)-4-(3-hydroxy-2-methylpropyl)piperidine-1-carboxylate (1.97 g, 5.0 mmol) and Dess-martin reagent (3.18 g) was stirred in dichloromethane (60 mL) at r.t for 16 hrs. The reaction mixture was quenched by adding 25% sodium bicarbonate solution (100 mL), then the mixture was extracted by EtOAc (60 mL×2). The organic phase was combined and concentrated to give a residue, which was further purified by a standard method to give the product (0.88 g). LC-MS: m/z 392.5 (M+H)+

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding 25% sodium bicarbonate solution (100 mL)
  3. extractionthe mixture was extracted by EtOAc (60 mL×2)
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas further purified by a standard method

Sources & evidence

ORD record
ord-4934398dbacb4102b379066e01b38f02
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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