Acetic Acid → tert-Butyl 4-(2-oxo-2,3-dihydro-1H-indol-1-yl)piperidine-1-carboxylate

HRID 967377

反応式

HRID 967377 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11]C)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:1]2[C:2]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:8][C:9]2=[O:11])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 5743389Methyl 2-aminobenzeneacetate

生成物 1

HCID 67472855tert-Butyl 4-(2-oxo-2,3-dihydro-1H-indol-1-yl)piperidine-1-carboxylate収率 130.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl 2-aminophenylacetate (3.0 g, 18.2 mmol) and 1-tert-butoxycarbonyl-4-piperidone (4.5 g, 22.6 mmol) were set stirring in 50 mL of CH2Cl2 under an atmosphere of nitrogen. Sodium triacetoxyborohydride (5.4 g, 25.5 mmol) was added followed by 1 mL of acetic acid. After 20 h at rt the mixture was quenched by the slow addition of saturated NaHCO3. After stirring for 30 min, the organics were separated, dried (MgSO4), and evaporated to afford 7.5 g of a purple oil. Purification by column chromatography (silica, 10-50% EtOAc/hexanes) gave 3.9 g (62%) of the title compound. TLC (silica, 25% EtOAc/hexanes): Rf=0.15. 1H NMR (400 MHz, CDCl3): 7.25 (m, 2H), 7.01 (m, 2H), 4.40 (m, 1H), 3.53 (s, 2H), 2.83 (m, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.51 (s, 9H).

後処理

  1. customAfter 20 h at rt the mixture was quenched by the slow addition of saturated NaHCO3
  2. customthe organics were separated
  3. dry with materialdried (MgSO4)
  4. customevaporated

出典と根拠

ORDレコード
ord-bfbb65c816a747f6b1f96984082eecfe
出典データセット
uspto-grants-2005_10
特許番号
US06953793B2

関連ノート

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