Triacetoxyperiodinane → tert-Butyl N-(3-oxopropyl)carbamate

HRID 2415051Notes

Reaction equation

HRID 2415051 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9](O)[CH2:10][CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:15]>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 12121609HCID 12121609, compound

Product 1

HCID 10910051tert-Butyl N-(3-oxopropyl)carbamateYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the N-t-butyloxycarbonyl-aminopropanol (15.0 g, 65.6 mmol) in dichloromethane (260 mL) at 0° C. was slowly added Dess-Martin periodinane reagent (47.3 g, 111 mmol). The mixture was allowed to gradually warm to ambient temperature and stirred overnight. It was then partitioned between diethyl ether (600 ml) and 1N sodium hydroxide (300 mL) and shaken vigorously. The organic layer was dried and evaporated. The residue was chromatographed on silica, eluting with 25% ethyl acetate/hexane to afford the product as a thin, colorless oil (4.20 g, 28%). 1H NMR (300 MHz, CDCl3) δ 9.63 (s, 1 H), 5.17 (br s, 1 H), 3.30 (q, 2 H), 2.60 (t, 2 H), 1.33 (s, 9 H).

Workup

  1. customat 0° C.
  2. customIt was then partitioned between diethyl ether (600 ml) and 1N sodium hydroxide (300 mL)
  3. stirringshaken vigorously
  4. customThe organic layer was dried
  5. customevaporated
  6. customThe residue was chromatographed on silica
  7. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c58786cd2f8343f49bbaadcefe02336b
Source dataset
uspto-grants-2004_11
Patent number
US06818643B1

Reaction notes

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