Water → 3-[(4-Chlorophenyl)(3-{2-fluoro-1-[3-fluoro-5-(hydroxymethyl)phenyl]-2-methylpropyl}azetidin-1-yl)methyl]benzonitrile

HRID 602990Notes

Reaction equation

HRID 602990 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=2)[N:9]2[CH2:12][CH:11]([CH:13]([C:18]3[CH:19]=[C:20]([CH:26]=[C:27]([F:29])[CH:28]=3)[C:21](OCC)=[O:22])[C:14]([F:17])([CH3:16])[CH3:15])[CH2:10]2)=[CH:4][CH:3]=1.[Li+].[BH4-].C(Cl)Cl.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([N:9]2[CH2:10][CH:11]([CH:13]([C:18]3[CH:19]=[C:20]([CH2:21][OH:22])[CH:26]=[C:27]([F:29])[CH:28]=3)[C:14]([F:17])([CH3:16])[CH3:15])[CH2:12]2)[C:30]2[CH:31]=[C:32]([CH:33]=[CH:34][CH:35]=2)[C:36]#[N:37])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4148881Lithium borohydrideHCID 67055325HCID 67055325, compound

Product 1

HCID 670554053-[(4-Chlorophenyl)(3-{2-fluoro-1-[3-fluoro-5-(hydroxymethyl)phenyl]-2-methylpropyl}azetidin-1-yl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the mixture of 42 mg (0.08 mmol) of ethyl 3-(1-{1-[(4-chlorophenyl)(3-cyanophenyl)methyl]azetidin-3-yl}-2-fluoro-2-methylpropyl)-5-fluorobenzoate in 3 mL of THF was added 0.18 mL (0.36 mmol) of 2 M LiBH4 solution in THF and the solution was stirred overnight at rt. Then it was poured into 20 mL of CH2Cl2 and 5 mL of water. The water layer was extracted with CH2Cl2 and the combined organic layer was concentrated. The residue was purified by silica gel chromatography with hexane/ethyl acetate to afford the title compound as a white solid; Mass Spectrum: m/e=481 (M+1, 35Cl), 483 (M+1, 37Cl).

Workup

  1. extractionThe water layer was extracted with CH2Cl2
  2. concentrationthe combined organic layer was concentrated
  3. customThe residue was purified by silica gel chromatography with hexane/ethyl acetate

Sources & evidence

ORD record
ord-bda4b8c24a4e40c0a53abdc04935ca30
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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