HCID 9837097, compound → HCID 86693773, compound

HRID 245059Notes

Reaction equation

HRID 245059 reaction equation
[N:1]([C@H:4]1[CH2:8][O:7][CH2:6][C@@H:5]1[O:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[N+]=[N-]>CC(C1C=C(C(C)(C)C)C(=O)/C(=C/N[C@H]2[C@H](N/C=C3/C=C(C(C)(C)C)C=C(C(C)(C)C)C/3=O)CCCC2)/C=1)(C)C.[Co].[Pd].C1COCC1>[CH3:11][Si:10]([CH3:13])([CH3:12])[O:9][C@H:5]1[CH2:6][O:7][CH2:8][C@@H:4]1[NH2:1]

Participants

5

Reactant 1

HCID 9837097HCID 9837097, compound

Product 1

HCID 86693773HCID 86693773, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178441016HCID 178441016, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [(3R,4S)-4-azidotetrahydrofuran-3-yl]oxy-trimethyl-silane (870 mg, 4.2 mmol; prepared according to the exact procedure found in Jacobsen, E. N.; Larrow, J. F.; Schaus, S. E. J. Org. Chem. 1997, 62, 4197-4199; except that commercially available (1R,2R)-(−)-1,2-cyclohexanediamino-N,N′-bis(3,5-di-t-butylsalicylidene)cobalt (II) is used as catalyst), 10% palladium on carbon (230 mg, 216 μmol), and THF (22 mL) is stirred at room temperature under hydrogen (60 psi) for 16 h. The reaction is filtered through a pad of diatomaceous earth and the pad is rinsed with THF (50 mL). The filtrate is concentrated in vacuo to give the title compound as a brown oil (825 mg, quantitative). LC-ES/MS m/z 176 (M+1).

Workup

  1. customprepared
  2. filtrationThe reaction is filtered through a pad of diatomaceous earth
  3. washthe pad is rinsed with THF (50 mL)
  4. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-dcac4546224b420c86e1a9e2ff7b94f0
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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