HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1692106
Notes
Print preview

Reaction equation

HRID 1692106 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F: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].O.C(O)(C(F)(F)F)=O>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:37][CH:38]=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]([OH:20])[CH2:16][CH2:15]2)[C:10]1=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66905541(R)-3-(3,5-Dichloro-4'-trifluoromethyl-biphenyl-4-ylmethyl)-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one

Product 1

HCID 57672044(R)-3-(3,5-Dichloro-4'-trifluoromethyl-biphenyl-4-ylmethyl)-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-oneYield 96.9%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (R)-3-(3,5-Dichloro-4′-trifluoromethyl-biphenyl-4-ylmethyl)-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one (0.12 g) in THF (6 mL), add water (6 mL) and TFA (2 mL). Stir the mixture at room temperature for 12 hours. Dilute the reaction mixture with ethyl acetate and wash with sodium bicarbonate (Sat.) and water. Separate the organic and dry over sodium sulfate, filter and concentrate. Purify the crude mixture on silica gel column with 50% ethyl acetate in hexane to 100% ethyl acetate to afford 0.088 g of the titled product. MS (m/z): 487 (M+).

Workup

  1. washwash with sodium bicarbonate (Sat.) and water
  2. customSeparate the organic and
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude mixture on silica gel column with 50% ethyl acetate in hexane to 100% ethyl acetate

Sources & evidence

ORD record
ord-e781cb2a3e604a52a464487548cef173
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153807B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes