HCID 89500369, compound → HCID 89500269, compound

HRID 245060Notes

Reaction equation

HRID 245060 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]>[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

3

Reactant 1

HCID 89500369HCID 89500369, compound

Product 1

HCID 89500269HCID 89500269, compound

Reagents, catalysts & solvents 1

HCID 178441017HCID 178441017, compoundCatalyst

Procedure

The title compound is prepared by essentially following the procedure described in Preparation 31 using [(3S,4R)-4-azidotetrahydrofuran-3-yl]oxy-trimethyl-silane (9.34 g, 46.4 mmol; prepared in opposing stereochemical configuration compared to the procedure found in Jacobsen, E. N.; Larrow, J. F.; Schaus, S. E. J. Org. Chem. 1997, 62, 4197-4199; except using commercially available (1S,2S)-(+)-1,2-cyclohexanediamino-N,N′-bis(3,5-di-t-butylsalicylidene)cobalt (II) as catalyst) to provide a colorless oil (7.55 g, 93%). LC-ES/MS m/z 176 (M+1).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-bfbbaee64dee4381b4c7632a3afb16af
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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