Triphenylphosphine → 3-Azido proline methyl ester

HRID 415871Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[C@H:8](O)[CH2:7][CH2:6][NH:5]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:58]=[N+:59]=[N-:60])(C2C=CC=CC=2)=O)C=CC=CC=1>>[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[CH:8]([N:58]=[N+:59]=[N-:60])[CH2:7][CH2:6][NH:5]1

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 199401P,P-Diphenylphosphinic azide

HCID 5363146Diisopropyl azodicarboxylate

HCID 45082777Methyl (3R)-3-hydroxy-L-prolinate

Product 1

HCID 591628253-Azido proline methyl ester

Procedure

Reaction of cis-3-hydroxyproline methyl ester with DIAD, triphenylphosphine and diphenylphosphoryl azide provides the desired 3-azido proline methyl ester. Transformation is typically carried out at low temperatures, e.g., 0° C., and after the addition, the reaction is allowed to warm to ambient temperature, e.g., about 25° C.

Sources & evidence

ORD record: ord-6063e1a0794c46b58c1eb2ace10ee284
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088804B2

Reaction notes

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