Triacetoxyperiodinane → Tert-butyl 3-formyl-4-methylpiperidine-1-carboxylate

HRID 1854355Notes

Reaction equation

HRID 1854355 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]([CH3:9])[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[CH:8]([CH3:9])[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:4]1)=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58009921Tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylate

Product 1

HCID 58010030Tert-butyl 3-formyl-4-methylpiperidine-1-carboxylateYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylate (2.58 g, 11.2 mmol, Preparation #S.1) in DCM (50 mL) was added Dess-Martin periodinane (5.73 g, 13.5 mmol). The reaction was stirred at ambient temperature for about 16 h before it was partitioned between EtOAc (150 mL) and saturated aqueous NaHCO3 (150 mL). The organic layer was filtered through Celite® then washed with saturated aqueous Na2CO3 (2×150 mL). The organic layer was separated and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to a constant weight to afford tert-butyl 3-formyl-4-methylpiperidine-1-carboxylate as a clear oil (1.49 g, 58%): LC/MS (Table 2, Method a) Rt=2.39 min; MS m/z: 228 (M+H)+.

Workup

  1. customwas partitioned between EtOAc (150 mL) and saturated aqueous NaHCO3 (150 mL)
  2. filtrationThe organic layer was filtered through Celite®
  3. washthen washed with saturated aqueous Na2CO3 (2×150 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to a constant weight

Sources & evidence

ORD record
ord-fbd6513ae1cb4bf1a75865134a4701ca
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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