Triphenylphosphine → Triphenylphosphine Oxide

HRID 552728Notes

Reaction equation

HRID 552728 reaction equation
ClC1N=CN=C2C=1N=CN2[C@H]1[C@@H]2[O:16]C(C)(C)O[C@@H]2[C@@H](CO)C1.C(NS(=O)=O)(OC(C)(C)C)=O.[C:34]1([P:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CCOC(C)=O>[C:47]1([P:40](=[O:16])([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10064860((3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanolHCID 178454374HCID 178454374, compound

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of ((3aR,4R,6R,6aS)-[6-(6-chloro-purin-9-yl)-2,2-dimethyltetrahydro-cyclopenta[1,3]dioxol-4-yl]-methanol (Yang, M.; Wei, Y.; Schneller, S. W. J. Org. Chem. 2004, 69, 3993-3996) (250.0 mg, 0.77 mmol), N-Boc-sulfonamide (226.6 mg, 1.16 mmol) and triphenylphosphine (242.3 mg, 0.92 mol) in EtOAc (8 mL) was added diisopropyl azodicarboxylate (227.3 μL, 1.16 mmol) dropwise as a solution in EtOAc (1 mL). The reaction was stirred at r.t. overnight, quenched with water and extracted with EtOAc. The organics were concentrated and the residue purified by flash chromatography (0 to 100% EtOAc/DCM) to obtain the product as an inseparable mixture with triphenylphosphine oxide. The material was carried on as such.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. concentrationThe organics were concentrated
  4. customthe residue purified by flash chromatography (0 to 100% EtOAc/DCM)

Sources & evidence

ORD record
ord-92f5bc84dbc246fb9bdcb1900addf900
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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