tert-Butyldimethylsilyl chloride → HCID 10540376, compound

HRID 1066018Notes

Reaction equation

HRID 1066018 reaction equation
[CH2:1]([C@@H:8]1[NH:11][C:10](=[O:12])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>C(Cl)Cl>[CH2:1]([C@@H:8]1[N:11]([Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C:10](=[O:12])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 10534985HCID 10534985, compound

Product 1

HCID 10540376HCID 10540376, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4(S)-benzylazetidin-2-one (400 mg, 2.48 mmol) in CH2Cl2 (8 mL) was added DIEA (648 μL, 3.72 mmol), followed by tert-butyldimethylsilyl chloride (411 mg, 2.73 mmol). The reaction mixture was stirred for 16 h at room temperature. The CH2Cl2 was evaporated and the residue was purified by flash chromatography (SiO2, 12% EtOAc in hexane) to give 4(S)-benzyl-1-(tert-butyldimethylsilyl)azetidin-2-one (647 mg, 95% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ7.34-7.15 (m, 5H), 3.77-3.70 (m, 1H), 3.25 (dd, J=13.5, 3.5 Hz, 1H), 2.99 (dd, J=15.5 Hz, 5 Hz, 1H), 2.70 (dd, J=15.5, 2.5 Hz, 1H), 2.59 (dd, J=13.5, 11 Hz, 1H), 1.01 (s, 9H), 0.31 (s, 3H), 0.29 (s, 3H).

Workup

  1. customThe CH2Cl2 was evaporated
  2. customthe residue was purified by flash chromatography (SiO2, 12% EtOAc in hexane)

Sources & evidence

ORD record
ord-318976bba11d48f9bd1223db708074ae
Source dataset
uspto-grants-2001_06
Patent number
US06242439B1

Reaction notes

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