Chloromethyl Methyl Ether → tert-butyl [(1R,2R)-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate

HRID 64433ノート

反応式

HRID 64433 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[OH:17])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)N[Si](C)(C)C.[K].C1(C)C=CC=CC=1.[CH3:36][O:37][CH2:38]Cl.[Cl-].[NH4+].C1[CH2:46][O:45][CH2:44]C1>C(OCC)(=O)C>[CH3:36][O:37][CH2:38][O:17][C@@H:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:8]1[N:7]([CH2:44][O:45][CH3:46])[C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 5

HCID 7864Chloromethyl Methyl Ether2 回HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 17998892(1R,2R)-N-Boc-1-amino-2-indanolHCID 131731101Potassium hexamethyldisilazane toluene2 回

生成物 1

HCID 86713447tert-butyl [(1R,2R)-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1 g of tert-butyl[(1R,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamate in 10 ml of THF was added 16.9 ml of a 0.5 M potassium hexamethyldisilazane/toluene solution at −78° C., followed by stirring for 30 minutes. 0.92 ml of chlorodimethyl ether was added thereto at −78° C., followed by warming to room temperature for 3 hours. 4 ml of a 0.5 M potassium hexamethyldisilazane/toluene solution and 0.31 ml of chlorodimethyl ether were added thereto at −78° C., followed by stirring at room temperature for 2 hours. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 311 mg of tert-butyl [(1R,2R)-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate.

後処理

  1. customat −78° C.
  2. customat −78° C.
  3. stirringby stirring at room temperature for 2 hours
  4. customa layer separation operation
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-78309252670e4d6fbe8ce6f3f33345cd
出典データセット
uspto-grants-2016_09
特許番号
US09447090B2

反応ノート

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