Ethyl oxoacetate → Ethyl 2-(1-(1-(4-chlorophenyl)cyclobutyl)-3-methylbutylamino]acetate

HRID 386929노트

반응식

HRID 386929 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([NH2:17])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]([NH:17][CH2:19][C:18]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 70211Ethyl oxoacetateHCID 134772DidesmethylsibutramineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 25050583Ethyl 2-(1-(1-(4-chlorophenyl)cyclobutyl)-3-methylbutylamino]acetate

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of cyclobutane amine 52a (0.68 g, 0.0027 mole) and ethyl glyoxylate (50% solution in toluene) (1.02 g, 0.01 mole) in 20 mL of a mixture of solvents DMF and acetic acid (ratio, 99:1) was added sodium triacetoxyborohydride (2.11 g, 0.01 mole) portion-wise over a period of 15 minutes at room temperature. The resulting mixture was stirred for 8 hours at room temperature and the progress of the reaction was monitored by TLC. The reaction mixture was poured in to saturated sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (50 mL×3). The combined extract was washed with water (50 mL), dried over sodium sulfate (Na2SO4) and evaporated. The residue was purified by silica gel column chromatography using 0-50% gradient of ethyl acetate and hexane as eluents to give pure 54a as colorless liquid in 45% (0.41 g) yield. The 1H NMR and mass spectral data are identical to the compound synthesized using the protocol described for the synthesis of 54a-e (Example 3, Scheme 7).

후처리

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. extractionThe combined extract
  3. washwas washed with water (50 mL)
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2caa4f9937584a4ea6ffe0029560707b
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372883B2

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