Ethanol → 4-(4-Amino-3-cyclohept-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1992033

反応式

HRID 1992033 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16](Br)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCO.[C:25]1(B(O)O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([C:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH:26]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 3434501Cyclohepten-1-ylboronic acidHCID 56834849tert-Butyl 4-(4-amino-3-bromophenyl)-piperidine-1-carboxylate

生成物 1

HCID 586945894-(4-Amino-3-cyclohept-1-enyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester収率 45.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

A solution of 230 mg (0.647 mmol) 4-(4-amino-3-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 6 mL toluene and 3 mL EtOH was treated with 118 mg (0.842 mmol) cyclohept-1-enylboronic acid and 2.60 mL (5.18 mmol) 2.0 M Na2CO3. The mixture was degassed via sonication, placed under Ar, treated with 52.3 mg (0.0453 mmol) Pd(PPh3)4, and heated to 85° C. for 23 h. The mixture was diluted with EtOAc (15 mL) and washed with water (1×15 mL) and brine (1×15 mL). The combined aqueous layers were extracted with EtOAc (15 mL), and the combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a Varian MegaBond Elut 50-gm column with 10-18% EtOAc-hexane afforded 108 mg (45%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C19H27N2O2, 315.2 (M−C4H9+2H), found 315.2.

後処理

  1. customThe mixture was degassed via sonication
  2. washwashed with water (1×15 mL) and brine (1×15 mL)
  3. extractionThe combined aqueous layers were extracted with EtOAc (15 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f35915574f234811b8d780d04c65d177
出典データセット
uspto-grants-2010_01
特許番号
US07645755B2

関連ノート

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