Acetic Acid → 4-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

HRID 2401115ノート

反応式

HRID 2401115 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.ClC(Cl)C.[CH3:13][O:14][C:15]([C:17]1([CH2:23][CH:24]=O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:13][O:14][C:15]([C:17]1([CH2:23][CH2:24][NH:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)=[O:16]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 706222-Amino-5-bromopyridineHCID 5049666Sodium triacetoxyborohydrideHCID 58468045methyl 4-(2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate

生成物 1

HCID 674786784-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-bromopyridin-2-amine (0.488 g, 2.82 mmol) in 1-2 dichloroethane (DCE, 10 mL) was added desired 4-(2-oxo-ethyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (0.529 g, 2.82), acetic acid (3.1 eq) and allowed to stir at room temperature for an hour. NaBH(OAc)3 (3 eq) was then added in one portion and reaction mixture allowed to stir at room temperature for 16 hours. The reaction mixture was then diluted with DCM (10 mL), quenched with 2 M of NH4OH in water. The aqueous layer was extracted with DCM (10 mL×2). The combined organic layers were washed with aqueous NaHCO3 (30 mL), brine (30 mL), and dried over Na2SO4, and concentrated under vacuum.

後処理

  1. stirringto stir at room temperature for 16 hours
  2. customquenched with 2 M of NH4OH in water
  3. extractionThe aqueous layer was extracted with DCM (10 mL×2)
  4. washThe combined organic layers were washed with aqueous NaHCO3 (30 mL), brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-1ce9037896ae4782af7e7b40aefd4a15
出典データセット
uspto-grants-2014_08
特許番号
US08796278B2

反応ノート

読み込み中…