Acetic Acid → 2-(4-Cyclopropyl-phenyl)-8-(3-phenyl-propyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1942216

반응식

HRID 1942216 반응식
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH2:14][CH2:13][C:12]4([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[C:11]3=[O:20])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C(O)(=O)C.[Na].[C:26]1([CH2:32][CH2:33][CH:34]=O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.O>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH2:14][CH2:13][C:12]4([CH2:19][CH2:18][N:17]([CH2:34][CH2:33][CH2:32][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH2:16][CH2:15]4)[C:11]3=[O:20])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7707BenzenepropanalHCID 5360545SodiumHCID 582872772-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

생성물 1

HCID 532338662-(4-Cyclopropyl-phenyl)-8-(3-phenyl-propyl)-2,8-diaza-spiro[4.5]decan-1-one수율 25%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 20 mg (0.074 mmol) 2-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one, 42 uL acetic acid, 44 mg (0.148 mmol) sodium triacetyoxyborohydride and excess 3-phenyl-propionaldehyde in 2 mL THF was stirred for at room temperature over night. Water was added, the mixture was extracted with ethyl acetate and the combined organic layers were evaporated to dryness. The residue was taken up in methanol and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 7.1 mg (25%) of the title compound. MS m/e: 389.4 [M+H]+.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. customthe combined organic layers were evaporated to dryness
  3. customsubjected to purification by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile, water and NEt3
  6. additionThe product containing fractions
  7. customwere evaporated

출처 및 근거

ORD 기록
ord-10015ebfb1cf410a8d8fbb3494b03f24
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389539B2

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