Chlorotrimethylsilane → HCID 68502098, compound

HRID 900508Notes

Reaction equation

HRID 900508 reaction equation
[OH:1][C@H:2]1[C@@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4][C:3]1=[O:12].C(N(CC)CC)C.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22].CCCCCCC>C1COCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:20][Si:21]([CH3:23])([CH3:22])[O:1][C@H:2]1[C@@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4][C:3]1=[O:12]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 8900HeptaneHCID 10219588cis-3-hydroxy-4-phenylazetidin-2-one

Product 1

HCID 68502098HCID 68502098, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Optically active (+)-cis-3-hydroxy-4-phenyl-azetidin-2-one (3.4 g, 20.8 mmol) was dissolved in THF (30 mL) along with triethylamine (5.8 g, 57.4 mmol) and DMAP (76 mg, 0.62 mmol) at 0° C. Trimethylsilyl chloride (2.4 g, 22 mmol) was added dropwise and the mixture stirred for 30 min. TLC (3:1 ethyl acetate:heptane) showed complete conversion to the less polar product. The mixture was diluted with ethyl acetate (30 mL), washed with saturated aqueous sodium bicarbonate (15 ml), brine (15 ml), and dried over sodium sulfate (5 g). The sodium sulfate was filtered and the filtrate was concentrated and solvent exchanged with heptane (50 mL) to give a white powder. The powder was collected via vacuum filtration through a Buchner funnel and dried under vacuum (<1 mmHg) at ambient temperature to a constant weight of 3.45 g (72% yield). mp: 120 to 122° C., [α]22578=+81.9 (MeOH,1.0), 1H NMR (400 MHz, CDCl3) δ (ppm): −0.08 (s, 9H), 4.79 (d, J=4.4 Hz, 1H), 5.09 (dd, J=4.4, 2.7 Hz, 1H), 6.16 (bm, 1H), 7.3 to 7.4 (m, 5H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (15 ml), brine (15 ml)
  2. dry with materialdried over sodium sulfate (5 g)
  3. filtrationThe sodium sulfate was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give a white powder
  6. filtrationThe powder was collected via vacuum filtration through a Buchner funnel
  7. customdried under vacuum (<1 mmHg) at ambient temperature to a constant weight of 3.45 g (72% yield)

Sources & evidence

ORD record
ord-5be0b1d64f9f43b88014470137666932
Source dataset
uspto-grants-2008_04
Patent number
US07358378B2

Reaction notes

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