Acetic Acid → N-(5-bromothiazol-2-yl)-cyclopropylmethylamine

HRID 1670536ノート

反応式

HRID 1670536 の反応式
C(O)(=O)C.[Br:5][C:6]1[S:10][C:9]([NH2:11])=[N:8][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:26]1([CH:29]=O)[CH2:28][CH2:27]1>C(Cl)Cl>[Br:5][C:6]1[S:10][C:9]([NH:11][CH2:29][CH:26]2[CH2:28][CH2:27]2)=[N:8][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 436002-Thiazolamine, 5-bromo-HCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 59822318N-(5-bromothiazol-2-yl)-cyclopropylmethylamine収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add acetic acid (2 mL, 33.4 mmol) to a mixture of 5-bromo-thiazol-2-ylamine (1 g, 5.6 mmol), sodium triacetoxyborohydride (3.5 g, 16.7 mmol) and cyclopropane carboxaldehyde (820 mg, 11.7 mmol) at room temperature under a nitrogen atmosphere. Stir the resulting solution for 1.5 h at ambient temperature. Dilute the solution with DCM (50 mL) and wash with saturated aqueous NaHCO3 (80 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (9:1 to 7:3 gradient) to obtain the title compound (970 mg, 75%). MS (ES+) m/z: 233.1 (M+).

後処理

  1. washwash with saturated aqueous NaHCO3 (80 mL)
  2. dry with materialDry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by chromatography on silica gel (40 g)
  6. washeluting with hexane/EtOAc (9:1 to 7:3 gradient)

出典と根拠

ORDレコード
ord-f3187df32cfd4517987610280afe49d7
出典データセット
uspto-grants-2011_08
特許番号
US07994163B2

反応ノート

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