Triphenylphosphine → HCID 57542543, compound

HRID 2080287Notes

Reaction equation

HRID 2080287 reaction equation
O[CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[NH:9]=[N+:10]=[N-:11].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>[N:9]([CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1)=[N+:10]=[N-:11]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24530Hydrazoic acidHCID 5363146Diisopropyl azodicarboxylateHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 57542543HCID 57542543, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (R)-5-(hydroxymethyl)pyrrolidin-2-one (660 mg, 5.73 mmol), hydrogen azide (10.8 mL, 8.60 mmol, 0.8 M in toluene), and PPh3 (2.25 g, 8.60 mmol) in THF was added DIAD dropwise. The mixture was stirred at rt for 1 h. LCMS indicated the completion of the reaction. The mixture was partially concentrated, filtered, and purified by RP-HPLC to give (R)-5-(azidomethyl)pyrrolidin-2-one (730 mg, 87%, 90% pure). LRMS (M+H+) m/z 141.1.

Workup

  1. customthe completion of the reaction
  2. concentrationThe mixture was partially concentrated
  3. filtrationfiltered
  4. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-09709de6d61a4e32b1ab4339eadef8c6
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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