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

Ammonium Chloride → Tert-butyl 3-[1-(3,5-difluorophenyl)-1-hydroxy-2,2-dimethylpropyl]azetidine-1-carboxylate

HRID 602702
Notes
Print preview

Reaction equation

HRID 602702 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)([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>C1COCC1>[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:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=[C:19]([F:21])[CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

HCID 67065877Tert-butyl 3-[1-(3,5-difluorophenyl)-1-hydroxy-2,2-dimethylpropyl]azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

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-06e5cc734c194ddf838c98867f1648cd
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906503B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes