Piperidine → HCID 54369926, compound

HRID 321947Notes

Reaction equation

HRID 321947 reaction equation
[Si:1]([N:8]1[C@@H:11]([CH2:12]I)[CH2:10][C:9]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[Si:1]([N:8]1[C@@H:11]([CH2:12][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:10][C:9]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8082PiperidineHCID 12944336HCID 12944336, compound

Product 1

HCID 54369926HCID 54369926, compoundYield 71%

Procedure

1-(tert-butyldimethylsilyl)-4(R)-(iodomethyl)-azetidin-2-one (202 mg, 0.62 mmol) was heated at reflux in piperidine (5 mL) for 2 h. The solution was concentrated, dissolved in CH2Cl2 and washed with saturated NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc) to give 1-(tert-butyldimethylsilyl)-4(R)-(piperidin-1-ylmethyl)azetidin-2-one (116 mg, 71% yield). 1H NMR (400 MHz, CDCl3) δ 3.70-3.63 (m, 1H), 3.16 (dd, J=15.3, 5.4 Hz, 1H), 2.70-2.61 (m, 2H), 2.45-2.26 (m, 5H), 1.60-1.53 (m, 4H), 1.46-1.38 (m, 2H), 0.96 (s, 9H), 0.24 (s, 6H).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-2934af24513443bda3f6f90cf48c9283
Source dataset
uspto-grants-2001_04
Patent number
US06211170B1

Reaction notes

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