Dimedone → HCID 58797594, 화합물

HRID 1593019노트

반응식

HRID 1593019 반응식
[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

참가 물질

5

반응물 2

HCID 31358Dimedone2회HCID 69448752HCID 69448752, 화합물

생성물 1

HCID 58797594HCID 58797594, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매2회HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-47224396d29f460785e85542ca9fd4f5
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294636B2

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