Lithium Chloride → Phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate

HRID 1842961ノート

反応式

HRID 1842961 の反応式
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[CH:18]([C:23](OC)=[O:24])[C:19](OC)=[O:20].[BH4-].[Na+].[Cl-].[Li+]>C(O)C.C1COCC1>[OH:24][CH2:23][CH:18]([C:3]1[CH:4]=[CH:5][C:6]([NH:8][C:9](=[O:10])[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:2]=1[F:1])[CH2:19][OH:20]

参加物

6

反応物 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 86672161Dimethyl 2-(2-fluoro-4-(phenoxycarbonylamino)phenyl)malonate

生成物 1

HCID 86672159Phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate収率 19%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of dimethyl 2-(2-fluoro-4-(phenoxycarbonylamino)phenyl)malonate (3.0 g, 8.31 mmol, 1.0 eq) in ethanol (15 mL) and THF (15 mL) was added NaBH4 (621 mg, 16.62 mmol, 2.0 eq) followed by lithium chloride (705 g, 16.62 mmol, 2.0 eq) at 0° C. and the mixture was stirred at 0° C. for 5 h. The solvent was evaporated and the residue diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by CC using MeOH/DCM (1:19) as eluent to get phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate (482 mg, 19%, white solid; TLC system: MeOH/DCM (1:9), Rf: 0.6)

後処理

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water (30 mL)
  3. extractionextracted with EtOAc (2×50 mL)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by CC

出典と根拠

ORDレコード
ord-2c55536ac0464644b2641751dfe9d37f
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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