Triethylamine → (3R*,4S*) N,N-Dimethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

HRID 862126ノート

反応式

HRID 862126 の反応式
Cl.[C:2]1([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]2[N:14]3[CH2:15][CH2:16][C@@H:11]([C@@H:12]([C:17](O)=[O:18])[CH2:13]3)[C:10]2=[O:20])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:28][NH:29][CH3:30].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:28][N:29]([CH3:30])[C:17]([C@@H:12]1[C@@H:11]2[CH2:16][CH2:15][N:14]([CH:9]([CH:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:10]2=[O:20])[CH2:13]1)=[O:18]

参加物

7

反応物 5

HCID 8471Triethylamine2 回HCID 10473Dimethylamine, hydrochlorideHCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 70115206(3R*,4S*)-6-Diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxylic acid hydrochloride

生成物 1

HCID 86752071(3R*,4S*) N,N-Dimethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A suspension of 46 (2.1 g, 6.6 mmol) and dimethylamine hydrochloride (0.65 g, 8.0 mmol) in DMF (30 ml) was treated with triethylamine (1.3 g, 13 mmol) at room temperature. To this suspension was added diethyl cyanophosphonate (1.2 g, 7.3 mmol) followed by triethylamine (0.67 g, 6.7 mmol) at room temperature. The mixture was stirred at room temperature for 5 hours, poured into NaHCO3 aq (50 ml) and extracted with EtOAc three times. The combined extracts were dried over Na2SO4 and concentrated. This mixture was purified by a column chromatography on silica gel (hexane:EtOAc=1:4) to give 47 as a single isomer at 3-position (1.4 g, 3.9 mmol, 60%)

後処理

  1. extractionextracted with EtOAc three times
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. customThis mixture was purified by a column chromatography on silica gel (hexane:EtOAc=1:4)

出典と根拠

ORDレコード
ord-530303c6fce344d68ba01f328f6f3c98
出典データセット
uspto-grants-1998_02
特許番号
US05716965

反応ノート

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