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Triphenylphosphine → 2(S)-Azido4-(5-chloro-2-pyridyl)-3(S)-phenylbutane

HRID 1160711
Notes
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Reaction equation

HRID 1160711 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@@H:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:10](O)[CH3:11])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:52]=[N+:53]=[N-:54])(C2C=CC=CC=2)=O)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:52]([C@H:10]([C@H:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)[CH3:11])=[N+:53]=[N-:54]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 234047044-(5-Chloro-2-pyridyl)-3(S)-phenyl-2(R)-butanol

Product 1

HCID 234047032(S)-Azido4-(5-chloro-2-pyridyl)-3(S)-phenylbutane

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a mixture of 4-(5-chloro-2-pyridyl)-3-phenyl-2-butanol (Step B, 0.24 g, 0.92 mmol), triphenylphosphine (1.5 g, 1.4 mmol) and diphenylphosphoryl azide (0.30 mL, 1.4 mmol) in 5 mL anhydrous THF was added diethylazodicarboxylate (0.24 mL, 1.4 mmol). After stirring at room temperature overnight, the resulting mixture was concentrated with silica gel (10 g) and the residue was loaded onto a silica gel column. Elution with 5 to 15% EtOAc in hexane afforded the title compound. 1H NMR (500 MHz, CD3OD): δ 8.35 (d, 1H), 7.52 (dd, 1H), 7.25-7.05 (m, 5H), 6.95 (d, 1H), 3.81 (m, 1H), 3.48 (m, 1H), 3.15-3.05 (m, 2H), 1.14 (d, 3H).

Workup

  1. concentrationthe resulting mixture was concentrated with silica gel (10 g)
  2. washElution with 5 to 15% EtOAc in hexane

Sources & evidence

ORD record
ord-e57d25520c384e8f97d35494c5ac88f1
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07816534B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes