1,2-Dichloroethane → tert-Butyl 3-(1-Pivaloyl-1H-indazol-5-ylamino)piperidine-1-carboxylate

HRID 656526ノート

反応式

HRID 656526 の反応式
O=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.ClCCCl.C(O)(=O)/C=C\C(O)=O.[NH2:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[N:32]=[CH:31]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)(O)[O-].[Na+]>[C:37]([N:33]1[C:34]2[C:30](=[CH:29][C:28]([NH:27][CH:2]3[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]3)=[CH:36][CH:35]=2)[CH:31]=[N:32]1)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 66716091HCID 66716091、化合物

生成物 1

HCID 59799788tert-Butyl 3-(1-Pivaloyl-1H-indazol-5-ylamino)piperidine-1-carboxylate収率 91%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
20 °C

実験手順

Into a 1 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer was added tert-butyl 3-oxopiperidine-1-carboxylate (14.2 g, 0.07 mol), 1,2-dichloroethane (300 mL), and 1-(5-amino-1H-indazol-1-yl)-2,2-dimethylpropan-1-one maleate salt (23.0 g, 0.07 mol). The vessel was purged with nitrogen and stirred at 20° C. for one hour. Sodium triacetoxyborohydride (19.0 g, 0.09 mol) was added, and the reaction was monitored by analytical TLC to completion. The reaction was diluted with 100 mL of saturated sodium bicarbonate. The organic phase was isolated, dried over MgSO4, filtered and evaporated to dryness to afford the title compound as a yellow solid (25.0 g, 91%).

後処理

  1. customInto a 1 L 3-neck round bottom flask fitted with a nitrogen inlet and mechanical stirrer
  2. customThe vessel was purged with nitrogen
  3. customThe organic phase was isolated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-a7ab0e6cb6d04ebf99499bc73d0326ad
出典データセット
uspto-grants-2011_12
特許番号
US08071779B2

反応ノート

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