Sodium borohydride → (R)-4-[(1-Methyl-2,2,2-trifluoro-ethylamino)-methyl]-benzylamine

HRID 1191007ノート

反応式

HRID 1191007 の反応式
[CH3:1][C@@H:2]([NH:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[C:3]([F:6])([F:5])[F:4].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[CH3:1][C@@H:2]([NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:15][CH:16]=1)[C:3]([F:5])([F:6])[F:4]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 59828823(R)-4-[(1-Methyl-2,2,2-trifluoro-ethylamino)-methyl]-benzonitrile

生成物 1

HCID 59828891(R)-4-[(1-Methyl-2,2,2-trifluoro-ethylamino)-methyl]-benzylamine収率 57%

試薬・触媒・溶媒 2

HCID 517166Dichlorocobalt hexahydrate触媒HCID 887Methanol溶媒

実験手順

Add cobalt(II) chloride hexahydrate (1.45 g, 6.09 mmol) to a solution of (R)-4-[(1-methyl-2,2,2-trifluoro-ethylamino)-methyl]-benzonitrile (695 mg, 3.045 mmol) in methanol (20 mL). Add sodium borohydride (1.15 g, 30.45 mmol) in small batches and stir at room temperature for 3 h. Quench with water, add chloroform and filter the mixture through Celite®. Separate layers and extract the aqueous phase twice with chloroform. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (40 g) eluting with a gradient of DCM to 19:1 and 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound as an oil (0.4 g, 57%). MS (ES+) m/z: 233 (M+H)+.

後処理

  1. customQuench with water
  2. additionadd chloroform
  3. filtrationfilter the mixture through Celite®
  4. extractionSeparate layers and extract the aqueous phase twice with chloroform
  5. dry with materialDry the combined organic extracts over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel (40 g)
  9. washeluting with a gradient of DCM to 19:1 and 9:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

出典と根拠

ORDレコード
ord-8ac68ba473c545fea86edb87522b3621
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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