Triacetoxyperiodinane → Tert-butyl 4-methyl-4-(3-oxopropoxy)piperidine-1-carboxylate

HRID 921140Notes

Reaction equation

HRID 921140 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1([CH3:19])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:19][C:6]1([O:5][CH2:4][CH2:3][CH:2]=[O:1])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 106938761Tert-butyl 4-(3-hydroxypropoxy)-4-methylpiperidine-1-carboxylate

Product 1

HCID 118307084Tert-butyl 4-methyl-4-(3-oxopropoxy)piperidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-hydroxypropoxy)-4-methylpiperidine-1-carboxylate (6.4 g, 23.41 mmol) in CH2Cl2 (300 mL) was added Dess-Martin Periodinane (10.43 g, 24.58 mmol) and the resulting mixture was stirred at room temp for 3 h. Sat. NaHCO3 solution was then added and the mixture was extracted with dichloromethane, dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (5-50% EtOAc/hexane) to afford tert-butyl 4-methyl-4-(3-oxopropoxy)piperidine-1-carboxylate (1.3 g, 4.79 mmol, 82% yield) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 9.82 (s, 1H), 3.84-3.57 (m, 4H), 3.13-3.02 (m, 2H), 2.66 (td, J=6.0, 1.8 Hz, 2H), 1.74 (d, J=12.8 Hz, 3H), 1.47 (s, 9H), 1.46-1.38 (m, 2H), 1.20 (s, 3H).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then purified by Biotage (5-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-c952b4ad28414675a577b9e64c98ea4c
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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