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

HRID 1692099ノート

反応式

HRID 1692099 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([N:41]3[CH2:46][CH2:45][CH:44]([C:47]([F:50])([F:49])[F:48])[CH2:43][CH2:42]3)=[O:40])=[CH:35][CH:34]=2)[CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][Si](C(C)C)(C(C)C)C(C)C)[CH2:16][CH2:15]2)[C:10]1=[O:31].C1COCC1.O.C(O)(C(F)(F)F)=O>C(OCC)(=O)C>[Cl:32][C:6]1[CH:5]=[C:4]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([N:41]3[CH2:46][CH2:45][CH:44]([C:47]([F:50])([F:48])[F:49])[CH2:43][CH2:42]3)=[O:40])=[CH:37][CH:38]=2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)[C:10]1=[O:31]

参加物

6

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 66904908(R)-3-[3,5-Dichloro-4'-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-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 76%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Treat a mixture of (R)-3-[3,5-dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one (0.34 g), THF (6 mL) and water (6 mL) with TFA (2 mL) at room temperature for 1 hour and at 50° C. for 2 hours. Cool the reaction, dilute with ethyl acetate, and wash with sodium bicarbonate (sat.). Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify on silica gel column with 100% ethyl acetate and 10% methanol in methylene chloride to afford 0.205 g (76%) of the titled product. MS (m/z): 598 (M+).

後処理

  1. additionTreat
  2. temperatureCool
  3. customthe reaction
  4. washwash with sodium bicarbonate (sat.)
  5. dry with materialDry the organic layer (Na2SO4)
  6. customremove the solvent in vacuo
  7. customto afford crude product
  8. custompurify on silica gel column with 100% ethyl acetate and 10% methanol in methylene chloride

出典と根拠

ORDレコード
ord-cf01e871c67f4a798b60e90b1361c1df
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…