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

HRID 1354524Notes

Reaction equation

HRID 1354524 reaction equation
[C:1]([NH:8][CH2:9][CH:10]([OH:13])CO)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>O>[C:1]([NH:8][CH2:9][CH:10]=[O:13])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

3

Reactant 1

HCID 4206999tert-butyl N-(2,3-dihydroxypropyl)carbamate

Product 1

HCID 4247255tert-butyl N-(2-oxoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(Boc-amino)-1,2-propanediol (21g, 110 mmol) was dissolved in water (200 ml) and stirred with potassium m-periodate (25.3g, 110 mmol) at room temperature under argon for 2h. The reaction mixture was filtered and washed with methylene chloride (100 ml). The aqueous layer was extracted with methylene chloride (3×150 ml). The organic extract was washed with brine (SOmI), dried and evaporated to dryness to give a light pink oil. This oil was purified by flash column chromatography using silica gel and CH2Cl2/ethyl acetate as the eluent. Yield was 14g (80%). 1HNMR (CDCl3) d 1.45 (s, 9H, t-Butyl), 4.08 (d, 2H, CH2), 5.24 (bs, 1H, NH) and 9.67 (s, 1H, CHO).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methylene chloride (100 ml)
  3. extractionThe aqueous layer was extracted with methylene chloride (3×150 ml)
  4. extractionThe organic extract
  5. washwas washed with brine (SOmI)
  6. customdried
  7. customevaporated to dryness
  8. customto give a light pink oil
  9. customThis oil was purified by flash column chromatography
  10. customYield

Sources & evidence

ORD record
ord-9de9cf8d890243268eae6552d8e31905
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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