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

HRID 133457Notes

Reaction equation

HRID 133457 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]

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 8028TetrahydrofuranSolvent

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-70649380935e425c9db3a18e966020f7
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Reaction notes

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