Benzyl chloroformate → (3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

HRID 16388

反応式

HRID 16388 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[NH:15][C@@H:14]([C@H:16]([OH:18])[CH3:17])[CH2:13][O:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].O.C(=O)(O)[O-].[Na+].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>O1CCCC1.O.C(OCC)(=O)C>[CH2:29]([O:28][C:26]([N:15]1[C@H:10]([C:4]2[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=2)[CH2:11][O:12][CH2:13][C@@H:14]1[C@H:16]([OH:18])[CH3:17])=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

7

反応物 3

HCID 10387Benzyl chloroformate2 回HCID 67374002(R)-1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]ethanolHCID 86585896Sodium bicarbonate water

生成物 1

HCID 67373415(3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (R)-1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]ethanol (2 g) in tetrahydrofuran (20 mL) was added saturated sodium bicarbonate water (20 mL) and benzyl chloroformate (1.31 mL). After stirring the reaction solution at room temperature for 16 hours, benzyl chloroformate (1.33 mL) was further added thereto, and the mixture was then stirred for another 20 hours. The resultant solution was diluted with water and ethyl acetate. The organic layer was partitioned, washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate), to thereby obtain the titled compound (880 mg). The physical properties of this crude product were as follows.

後処理

  1. stirringthe mixture was then stirred for another 20 hours
  2. customThe organic layer was partitioned
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-a67cc7744e6c493b8540664ed49f314e
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

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