Triphenylphosphine → tert-Butyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

HRID 1896214Notes

Reaction equation

HRID 1896214 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:12]=[C:10]1[C@@H:9]2[CH2:13][C@@H:14]([CH2:15][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[O:16]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 11252852tert-Butyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline (100 g, 0.443 mol) and PPh3 (227 g, 0.866 mol) in dry THF (1 L) was added dropwise DEAD (151 g, 0.866 mol) at 0° C. under nitrogen. After the addition, the reaction was allowed to warm up to room temperature and stirred overnight. The reaction was concentrated in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1˜5:1) which gave the title compound Va as a yellow solid (106.5 g).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1˜5:1) which

Sources & evidence

ORD record
ord-6e7ad2a9daa444528db4557935a21a9d
Source dataset
uspto-grants-2013_08
Patent number
US08518952B2

Reaction notes

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