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

HRID 1942216

反応式

HRID 1942216 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-10015ebfb1cf410a8d8fbb3494b03f24
出典データセット
uspto-grants-2013_03
特許番号
US08389539B2

関連ノート

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