Sodium triacetoxyborohydride → (R)-3-[3,5-Dichloro-4'-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one

HRID 1692117ノート

反応式

HRID 1692117 の反応式
[NH2:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[CH:11]=[C:12]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([N:33]3[CH2:38][CH2:37][CH:36]([C:39]([F:42])([F:41])[F:40])[CH2:35][CH2:34]3)=[O:32])=[CH:27][CH:26]=2)[CH:13]=[C:14]([Cl:24])[C:15]=1[CH2:16][C@@H:17]1[CH2:21][CH:20](O)[O:19][C:18]1=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[Cl:24][C:14]1[CH:13]=[C:12]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([N:33]3[CH2:38][CH2:37][CH:36]([C:39]([F:42])([F:41])[F:40])[CH2:35][CH2:34]3)=[O:32])=[CH:29][CH:30]=2)[CH:11]=[C:10]([Cl:9])[C:15]=1[CH2:16][C@@H:17]1[CH2:21][CH2:20][N:1]([N:2]2[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]2)[C:18]1=[O:19]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 121256451-Aminopiperidin-4-OLHCID 57672055(R)-3-[3,5-Dichloro-4'-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-5-hydroxy-dihydro-furan-2-one

生成物 1

HCID 17751083(R)-3-[3,5-Dichloro-4'-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one収率 20.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

Dissolve 1-Amino-piperidin-4-ol (0.204 g, 1.1 eq.) in acetonitrile (3 mL) and heat the solution to 50° C. When the temperature reaches 35° C., add (R)-3-[3,5-Dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-5-hydroxy-dihydro-furan-2-one (0.829 g, 1 eq.) and continue heating to 50° C. for 1 hour. Allow the reaction to cool to room temperature and add sodium triacetoxyborohydride (0.508 g, 1.5 eq.). Allow the reaction to stir overnight at room temperature. Add water and extract with EtOAc. Remove the solvent and chromatograph the residue on silica gel to afford 200 mg of the titled compound. MS (m/z): 598 (M+1, 35Cl), 600 (M+1, 37Cl).

後処理

  1. customreaches 35° C.
  2. temperaturecontinue heating to 50° C. for 1 hour
  3. customthe reaction
  4. temperatureto cool to room temperature
  5. customthe reaction
  6. extractionAdd water and extract with EtOAc
  7. customRemove the solvent and chromatograph the residue on silica gel

出典と根拠

ORDレコード
ord-b8b15bbf0f64454693c7ad9416da9e28
出典データセット
uspto-grants-2012_04
特許番号
US08153807B2

反応ノート

読み込み中…