Triphenylphosphine → (3R)-1-(Benzyloxy)-3-butylazetidin-2-one

HRID 1396861Notes

Reaction equation

HRID 1396861 reaction equation
O[CH2:2][C@@H:3]([CH2:15][CH2:16][CH2:17][CH3:18])[C:4]([NH:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:15]([C@@H:3]1[CH2:2][N:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]1=[O:5])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 16037944(2R)-N-(Benzyloxy)-2-(hydroxymethyl)hexanamide

Product 1

HCID 16037946(3R)-1-(Benzyloxy)-3-butylazetidin-2-oneYield 110%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]hexanamide (6) (52 g, 0.21 mol) and Ph3P (60 g, 0.23 mol) in THF (1500 mL) at 0° C. was added DIAD (41.8 g, 0.21 mol). The mixture was warmed up to rt and stirred overnight. TLC indicated completion of the reaction. THF was removed under vacuum. The residue was titurated with ethyl acetate/petroleum ether (1:10) and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography to provide the title compound (52.8 g, 110%). LCMS: (M+H)+: 234.2.

Workup

  1. customcompletion of the reaction
  2. customTHF was removed under vacuum
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-854be2330a174304af21c4392882ecd9
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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