Stannanecarbonitrile, tributyl- → 3-{(R*)-1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]-piperidin-3-yl}-benzonitrile

HRID 2365966ノート

反応式

HRID 2365966 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]2[CH:19]=[C:20](OS(C(F)(F)F)(=O)=O)[CH:21]=[CH:22][CH:23]=2)[CH2:13]1.C([Sn]([C:45]#[N:46])(CCCC)CCCC)CCC>ClCCCl.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>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:45]#[N:46])[CH2:13]1

参加物

5

反応物 2

HCID 200512Stannanecarbonitrile, tributyl-HCID 86644712Trifluoromethanesulfonic acid 3-{(R*)-1-[(S)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]-piperidin-3-yl}phenyl ester

生成物 1

HCID 251751673-{(R*)-1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]-piperidin-3-yl}-benzonitrile収率 7.6%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of trifluoromethanesulfonic acid 3-{(R*)-1-[(S)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]-piperidin-3-yl}phenyl ester (51 mg, 0.11 mmol), tributyltin cyanide (142 mg, 0.45 mmol) and tetrakis(triphenylphosphine)palladium (189 mg, 0.164 mmol) in 1,2-dichloroethane (15 ml) was heated in a microwave reactor at 80° C. for 80 h. The solid precipitate was filtered off and the mixture was evaporated to dryness. The residue was redissolved in DCM, filtered and washed two times with 1 M HCl. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness. The crude product was purified by flash chromatography first using gradient of DCM and MeOH and then using gradient of heptane and EtOAc as eluent to give 2.8 mg of the title compound.

後処理

  1. filtrationThe solid precipitate was filtered off
  2. customthe mixture was evaporated to dryness
  3. dissolutionThe residue was redissolved in DCM
  4. filtrationfiltered
  5. washwashed two times with 1 M HCl
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated to dryness
  9. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-727ffd88c0aa45c89a81b370a3641c9e
出典データセット
uspto-grants-2014_04
特許番号
US08697723B2

反応ノート

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