tert-butyl N-(2,3-dihydroxypropyl)carbamate → tert-butyl N-(2-oxoethyl)carbamate

HRID 899700Notes

Reaction equation

HRID 899700 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH:9]([OH:12])CO)([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+]>O>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH:9]=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4206999tert-butyl N-(2,3-dihydroxypropyl)carbamateHCID 23667635Sodium periodate

Product 1

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of (2,3-dihydroxy-propyl)-carbamic acid tert-butyl ester (0.955 g, 5.00 mmol) in water (12 mL) was added sodium periodate (2.35 g, 11.0 mmol). The mixture was stirred at room temperature for 1 h and then extracted with dichloromethane (3×10 mL). The extracts were dried over Na2SO4 and concentrated to give (2-oxo-ethyl)-carbamic acid tert-butyl ester as a colorless liquid (778 mg, 98%). 1H NMR (CDCl3) δ 1.45 (s, 9H), 4.07 (d, J=4.5 Hz, 2H), 5.20 (brs, 1H), 9.65 (s, 1H).

Workup

  1. extractionextracted with dichloromethane (3×10 mL)
  2. dry with materialThe extracts were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-51f1dedff1294e4f85bc4b09e8dae88c
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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