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

Tetrahydrofuran → Tert-butyl 3-[1-(3,5-difluorophenyl)-1-hydroxy-2,2-diethylpropyl]azetidine-1-carboxylate

HRID 1724210
Notes
Print preview

Reaction equation

HRID 1724210 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:5]([CH:7]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=[O:6].[C:22]([Mg]Cl)(C)(C)[CH3:23].[NH4+].[Cl-].[CH2:30]1[CH2:34]O[CH2:32][CH2:31]1>>[F:1][C:2]1[CH:3]=[C:4]([C:5]([CH:7]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:8]2)([OH:6])[C:31]([CH2:22][CH3:23])([CH2:30][CH3:34])[CH3:32])[CH:18]=[C:19]([F:21])[CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 670659051,1-Dimethylethyl 3-(3,5-difluorobenzoyl)-1-azetidinecarboxylateHCID 178418310HCID 178418310, compound

Product 1

HCID 69057678Tert-butyl 3-[1-(3,5-difluorophenyl)-1-hydroxy-2,2-diethylpropyl]azetidine-1-carboxylate

Conditions

Temperature
-78 °C

Procedure

To a solution of 3.07 g (10.34 mmol) of tert-butyl 3-(3,5-difluorobenzoyl)azetidine-1-carboxylate in 20 mL of THF, 36.19 mL (36.19 mmol) of tert-butyl magnesium chloride was added and stirred for 3.5 h at −78° C. To the solution was added 8 mL of aq. NH4Cl and the solution was filtered to remove the solid. The filtrate was washed with ether. The combined organic layer was concentrated to remove solvents and residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound; 1H-NMR(CDCl3) δ 0.897 (s, 9H), 1.425 (s, 9H), 2.234(br, 1H), 3.25 (m, 1H), 3.55 (m, 1H), 3.71 (t, J=8.9 Hz, 1H), 3.97 (t, J=8.4 Hz, 1H), 4.17(m ,1H), 6.53-6.74 (m, 3H).

Workup

  1. filtrationthe solution was filtered
  2. customto remove the solid
  3. washThe filtrate was washed with ether
  4. concentrationThe combined organic layer was concentrated
  5. customto remove solvents and residue
  6. customwas purified by silica gel chromatography with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-bc3320d818bb4b5c9719c03e656f66c9
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07485732B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes