Methanol → HCID 58119773, compound

HRID 2368639Notes

Reaction equation

HRID 2368639 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]3[C:21]4([CH2:37]CC[CH:34]4I)[O:22][CH:23]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)[C:12]3=[C:11]([CH:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C.N(C(C)(C)C#N)=NC(C)(C)C#N.CO>C1(C)C=CC=CC=1>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][CH:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]3[C:21]([CH3:34])([CH3:37])[O:22][CH:23]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=4)[C:12]3=[C:11]([CH:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[C:10]1=2)([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 6547AzobisisobutyronitrileHCID 123134Tris(trimethylsilyl)silaneHCID 58119785HCID 58119785, compound

Product 1

HCID 58119773HCID 58119773, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 mg 8-(tert-Butyl-dimethyl-silanyloxy)-9-cyclopentyl-3-iodomethyl-3,6,6-trimethyl-1-(4-trifluoromethyl-phenyl)-1,3,5,6,7,8-hexahydro-furo[3,4-b]quinoline (example XXI) are dissolved in 1 ml toluene and mixed successively under argon with 300 μl tris-trimethylsilyl-silane and 1 mg azo-bis-isobutyro-nitrile. The reaction mixture is heated for 4 hours to 110° C. and for 12 hours at room temperature. After addition of 1 ml methanol the solvents are evaporated in vacuo and the residue is partitioned between water and ethylacetate. The aqueous phase is extracted twice with ethylacetate and the combined organic phases are washed with brine. After drying with magnesium sulphate the solvents are evaporated in vacuo. The crude product thus obtained is directly submitted to the next step (example 1 (4)).

Workup

  1. customare evaporated in vacuo
  2. customthe residue is partitioned between water and ethylacetate
  3. extractionThe aqueous phase is extracted twice with ethylacetate
  4. washthe combined organic phases are washed with brine
  5. dry with materialAfter drying with magnesium sulphate the solvents
  6. customare evaporated in vacuo

Sources & evidence

ORD record
ord-e90bd49776a747d0b04fd16228534d2e
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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