Solketal → HCID 22603438, compound

HRID 2307925Notes

Reaction equation

HRID 2307925 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[N+](=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N-]>ClC(Cl)C.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 7528SolketalHCID 6577053H-Indole-2-carboxylic acid, 3-diazo-, ethyl ester

Product 1

HCID 22603438HCID 22603438, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

Rhodium acetate dimer (30 mg) was added to a solution of solketal (0.87 ml) and ethyl 3-diazoindole-2-carboxylate (3 mg) in dichloroethane (10 ml), and stirred at 85° C. for 3 hours. The reaction was concentrated in vacuo and the residue purified by column chromatography using a gradient of 0% to 20% ethyl acetate:iso-hexane as eluent to afford the product as a pale yellow solid (435 mg, 97%); NMR d (CD3SOCD3) 1.27-1.38 (m, 9H), 3.88 (m, 1H), 4.11 (m, 3H), 4.30 (q, 2H), (m, 1H), 7.01 (t, 1H), 7.24 (t, 1H), 7.36 (d, 1H), 7.65 (d, 1H), 11.27 (s, 1H); M/z (+) 320.3 (MH+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-772933a95e8f4f589e58df47182dcbbf
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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