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

HRID 862126노트

반응식

HRID 862126 반응식
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]

참가 물질

7

반응물 5

HCID 8471Triethylamine2회HCID 10473Dimethylamine, hydrochlorideHCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 70115206(3R*,4S*)-6-Diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxylic acid hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-530303c6fce344d68ba01f328f6f3c98
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716965

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