Toluene → 1-Oxa-7-azaspiro[4.4]nonane-7-carboxylic acid, 4,4-dimethyl-, 1,1-dimethylethyl ester

HRID 504436Notes

Reaction equation

HRID 504436 reaction equation
I[CH:2]1[C:6]([CH3:8])([CH3:7])[C:5]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)[O:4][CH2:3]1.C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C.N(C(C)(C)C#N)=NC(C)(C)C#N.C1(C)C=CC=CC=1>>[CH3:7][C:6]1([CH3:8])[C:5]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 6547AzobisisobutyronitrileHCID 123134Tris(trimethylsilyl)silaneHCID 666625521-Oxa-7-azaspiro[4.4]nonane-7-carboxylic acid, 3-iodo-4,4-dimethyl-, 1,1-dimethylethyl ester

Product 1

HCID 666619971-Oxa-7-azaspiro[4.4]nonane-7-carboxylic acid, 4,4-dimethyl-, 1,1-dimethylethyl ester

Conditions

Temperature
90 °C

Procedure

A mixture of tert-butyl 3-iodo-4,4-dimethyl-1-oxa-7-azaspiro[4.4]nonane-7-carboxylate (0.47 g, 0.0012 mol), tris(trimethylsilyl)silane (0.456 mL, 0.00148 mol) and 2,2′-azo-bis-isobutyronitrile (0.002 g, 0.00001 mol) in toluene (10.00 mL, 0.09388 mol) was heated at 90° C. overnight. The volatiles were removed in-vacuo and the residue was purified by CombiFlash, eluting with 0 to 30% EtOAc in hexane, to provide the THF compound. LCMS (M+Na) 278.2.

Workup

  1. customThe volatiles were removed in-vacuo
  2. customthe residue was purified by CombiFlash
  3. washeluting with 0 to 30% EtOAc in hexane
  4. customto provide the THF compound

Sources & evidence

ORD record
ord-c7308bcccfcd4bb19917f622c7444506
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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