Dimedone → HCID 58797594、化合物

HRID 1593019ノート

反応式

HRID 1593019 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[S:8][CH:9]=[C:10]([CH:12]3[CH2:17][CH2:16][N:15](C(OCC=C)=O)[CH2:14][CH2:13]3)[N:11]=2)=[CH:4][CH:3]=1.CC1(C)CC(=O)CC(=O)C1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[S:8][CH:9]=[C:10]([CH:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[N:11]=2)=[CH:24][CH:25]=1

参加物

5

反応物 2

HCID 31358Dimedone2 回HCID 69448752HCID 69448752、化合物

生成物 1

HCID 58797594HCID 58797594、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of allyl 4-[2-(4-chlorobenzyl)-1,3-thiazol-4-yl]piperidine-1-carboxylate (692 mg) in anhydrous THF (20 ml) was added dimedone (2.06 g) followed by Pd(PPh3)4 (201 mg) and the resulting mixture was stirred at room temperature for 4 hours. A further portion of dimedone (1.03 g) and Pd(PPh3)4 (100 Mg) was added and the mixture was stirred for a further 18 hours. The reaction mixture was partitioned between 1N sodium hydroxide (50 ml) and ethyl acetate (100 ml). The organics were separated, dried and evaporated to dryness. The residue was purified by column chromatography on SCX-2 stationary phase using a gradient of DCM up to 50% 7N NH3 in MeOH in dichloromethane as eluent to give 4-[2-(4-chlorobenzyl)-1,3-thiazol-4-yl]piperidine as a solid. Yield 162 mg). NMR (CDCl3): 1.8 (m, 2H), 2.2 (m, 2H), 2.4 (bs, 1H), 2.8-3.0 (m, 3H), 3.3 (m, 2H), 4.4 (s, 2H), 7.4 (m, 5H).

後処理

  1. stirringthe mixture was stirred for a further 18 hours
  2. customThe reaction mixture was partitioned between 1N sodium hydroxide (50 ml) and ethyl acetate (100 ml)
  3. customThe organics were separated
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on SCX-2 stationary phase

出典と根拠

ORDレコード
ord-47224396d29f460785e85542ca9fd4f5
出典データセット
uspto-grants-2007_11
特許番号
US07294636B2

反応ノート

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