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 1692117노트

반응식

HRID 1692117 반응식
[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]

참가 물질

5

반응물 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

생성물 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-one수율 20.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b8b15bbf0f64454693c7ad9416da9e28
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153807B2

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