Triphenylphosphine → Benzyl (3S)-3-(azidomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 515882Notes

Reaction equation

HRID 515882 reaction equation
O[CH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C1(P([N:37]=[N+:38]=[N-:39])(C2C=CC=CC=2)=O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N:37]([CH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[N+:38]=[N-:39]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 12114557benzyl (3S)-3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 131733307Benzyl (3S)-3-(azidomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound is obtained using a protocol from the literature (D. Pagé et al J. Med. Chem, 44, 2387, 2001) starting from 23 g of the compound obtained in Step A (77.3 mmol) in the presence of diphenylphosphoryl azide and triphenylphosphine in solution in THF. After purification by chromatography over silica gel using petroleum ether and ethyl acetate as eluants, the title product is obtained in the form of an oil.

Workup

  1. customThis compound is obtained
  2. customAfter purification by chromatography over silica gel

Sources & evidence

ORD record
ord-9c3357063bca42d68aa175a1623638e0
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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