Imidazole → 1-Benzhydryl-3-(tert-butyldiphenylsilyloxy)azetidine

HRID 1092993Notes

Reaction equation

HRID 1092993 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:24]([Si:28](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:27])([CH3:26])[CH3:25].O>CN(C=O)C>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 178424121-Benzhydryl-3-(tert-butyldiphenylsilyloxy)azetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1-Benzhydrylazetan-3-ol (2.0 g, 8.4 mmol) in DMF (20 ml) at 0° C. is treated with imidazole (0.57 g, 8.4 mmol) and t-butylchlorodiphenyl silane (2.31 g, 8.4 mmol). The reaction mixture is allowed to warm up to room temperature and stirred overnight. The mixture is poured into water (250 ml) and extracted with EtOAc (3×100 ml). The combined organic extracts are washed with water (2×100 ml), brine (100 ml) and dried over MgSO4. The solvent is removed in vacuo to yield the titled compound.

Workup

  1. extractionextracted with EtOAc (3×100 ml)
  2. washThe combined organic extracts are washed with water (2×100 ml), brine (100 ml)
  3. dry with materialdried over MgSO4
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e3cab940e2154c0a9282c003419ec02f
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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