Imidazole → 3-((Tert-butyldiphenylsilyl)oxy)azetidine

HRID 1429730Notes

Reaction equation

HRID 1429730 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.N1C=CN=C1.[CH3:12][C:13]([Si:16](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:15])[CH3:14]>C(Cl)Cl.O>[Si:16]([O:6][CH:4]1[CH2:5][NH:2][CH2:3]1)([C:13]([CH3:15])([CH3:14])[CH3:12])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 178425313-((Tert-butyldiphenylsilyl)oxy)azetidineYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of azetidin-3-ol hydrochloride (5.11 g, 46.7 mmol, 1.0 equiv) and 1H-imidazole (9.52 g, 140 mmol, 3.0 equiv) in DCM (100 mL) at 0° C. was added TBDPSCl (19.18 g, 70 mmol, 1.5 equiv) dropwise. The resulting mixture was stirred at rt overnight and then diluted with water, and extracted with DCM. The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude product was eluted over a silica gel with DCM/MeOH=100/1 to 10/1 to give 12 g of 3-(tert-butyldiphenylsilyloxy) azetidine as a colorless oil.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. washThe crude product was eluted over a silica gel with DCM/MeOH=100/1 to 10/1

Sources & evidence

ORD record
ord-6e171ae527654a20b8f62abe14b6873f
Source dataset
uspto-grants-2015_01
Patent number
US08940744B2

Reaction notes

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