Triacetoxyperiodinane → Tert-butyl [(6-chloropyridin-3-yl)methyl](3-oxopropyl)carbamate

HRID 552914Notes

Reaction equation

HRID 552914 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:17][CH2:18][CH2:19][OH:20])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:17][CH2:18][CH:19]=[O:20])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86632446Tert-butyl [(6-chloropyridin-3-yl)methyl](3-hydroxypropyl)carbamate

Product 1

HCID 86632445Tert-butyl [(6-chloropyridin-3-yl)methyl](3-oxopropyl)carbamateYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.00 g (9.97 mmol) of tert-butyl [(6-chloropyridin-3-yl)methyl](3-hydroxypropyl)carbamate are dissolved in 50 ml of dichloromethane, 56.38 g (19.94 mmol) of a 15 percent strength solution of Dess-Martin periodinane in dichloromethane are added and the mixture is stirred at room temperature for 1 hour. The reaction mixture is washed with 1N aqueous sodium hydroxide solution and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (1:1) gives 2.75 g (92% of theory) of tert-butyl [(6-chloropyridin-3-yl)methyl](3-oxopropyl)carbamate.

Workup

  1. washThe reaction mixture is washed with 1N aqueous sodium hydroxide solution
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-e218f26f664e4565a0807f3d7f67b8da
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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