Nitrogen → HCID 68069606, compound

HRID 2280370Notes

Reaction equation

HRID 2280370 reaction equation
N#N.[I:3][CH:4]1[CH:9]2[O:10][C:11](=[O:12])[CH:7]3[CH:8]2[C:13]2([CH2:15][CH2:14]2)[CH:5]1[CH:6]3[C:16]([OH:18])=[O:17].[CH3:19][Si](C=[N+]=[N-])(C)C>CO>[I:3][CH:4]1[CH:9]2[O:10][C:11](=[O:12])[CH:7]3[CH:8]2[C:13]2([CH2:15][CH2:14]2)[CH:5]1[CH:6]3[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 947NitrogenHCID 167693TrimethylsilyldiazomethaneHCID 67615825HCID 67615825, compound

Product 1

HCID 68069606HCID 68069606, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 6-iodo-2-oxohexahydrospiro[3,5-methanocyclopenta[b]furan-4,1-cyclopropane]-7-carboxylic acid (5.00 g, 14.96 mmol) in dry MeOH (75 mL) was added TMSCH2N2 (2.0 M in hexanes, 37.0 mL, 74.83 mmol). The reaction mixture was stirred at rt overnight, concentrated under reduced pressure and purified by FC (hept/EA, 4:1) to give the title compound as a white solid. TLC: rf (hept/EA, 4:1)=0.18.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by FC (hept/EA, 4:1)

Sources & evidence

ORD record
ord-175eef0bd7c945da9db1a469783917ad
Source dataset
uspto-grants-2015_09
Patent number
US09139524B2

Reaction notes

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