(3S)-pyrrolidin-3-ol → (S)-4-[4-(3-hydroxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-yloxymethyl]-benzonitrile

HRID 2415502ノート

反応式

HRID 2415502 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:22])[CH:3]=1.[OH:23][C@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1>>[OH:23][C@H:24]1[CH2:28][CH2:27][N:26]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:12][CH2:13][C:14]4[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=4)=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:22])[CH:3]=2)[CH2:25]1

参加物

3

反応物 2

HCID 2733874(3S)-pyrrolidin-3-olHCID 22641336HCID 22641336、化合物

生成物 1

HCID 10109108(S)-4-[4-(3-hydroxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-yloxymethyl]-benzonitrile収率 87.7%

実験手順

A solution of 1.42 g of (4.6 mmol) of 4-(4-chloro-2-methyl-quinolin-7-yloxymethyl)-benzonitrile and 1.11 g (12.5 mmol) of (S)-3-hydroxypyrrolidine in 1-methyl-2-pyrrolidine (25 ml) was heated under nitrogen at 100° C. (oil bath temperature) for 23 h. The reaction mixture was concentrated in a high vacuum, the residue taken up in methylene chloride, which was washed with water, saturated NaCl solution and then dried over magnesium sulphate. The solvent was removed in vacuo, the residue triturated with MeOH, filtered off by suction, washed subsequently with MeOH and ether and then dried in a high vaccum to give 1.45 g (83.86%) of the (S)-4-[4-(3-hydroxy-pyrrolidin-1-yl)-2-methyl-quinolin-7-yloxymethyl]-benzonitrile as a brown solid. ISP mass spectrum, m/e: 360.2 (M+1 calculated for C22H21N3O2: 360.2).

後処理

  1. concentrationThe reaction mixture was concentrated in a high vacuum
  2. washwhich was washed with water, saturated NaCl solution
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customthe residue triturated with MeOH
  6. filtrationfiltered off by suction
  7. washwashed subsequently with MeOH and ether
  8. customdried in a high vaccum

出典と根拠

ORDレコード
ord-491498adb21a4df6ad5b9f86b9b0001b
出典データセット
uspto-grants-2004_11
特許番号
US06818767B2

反応ノート

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