Diazomethane → HCID 10828432, compound

HRID 1066024Notes

Reaction equation

HRID 1066024 reaction equation
[CH2:1]([C@@H:8]1[N:11]([Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:10](=[O:19])[C@H:9]1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:23])=[N-]>CCOCC>[CH2:1]([C@@H:8]1[N:11]([Si:12]([C:15]([CH3:17])([CH3:16])[CH3:18])([CH3:13])[CH3:14])[C:10](=[O:19])[C@H:9]1[O:20][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 20659833HCID 20659833, compound

Product 1

HCID 10828432HCID 10828432, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4(S)-benzyl-1-(tert-butyldimethyl-silyl)-3(S)-hydroxyazetidin-2-one (150 mg, 0.51 mmol) in Et2O (70 mL) at 0° was added silica gel (40-60 μm, 9 g). The vigorously stirred mixture was treated with diazomethane in Et2O (50 mL, 0.3-0.5 M solution). Once the yellow color had almost disappeared after about 15 min, additional diazomethane solution (20 mL) was added. This procedure was repeated several times until no more starting material could be detected on TLC (about 1.5 h). The reaction mixture was stirred for an additional hour at room temperature then filtered and concentrated to give 4(S)-benzyl-1-(tert-butyl-dimethylsilyl)-3(S)-methoxyazetidin-2-one (157 mg, 99% yield) as a white solid which was pure enough for further manipulation. 1H-NMR (400 MHz, CDCl3) δ7.27-7.20 (m, 5H), 4.16 (d, J=1.9 HZ, 1H), 3.67 (ddd, J=11.1, 3.8, 1.9 Hz, 1H), 3.23 (dd, J=13.5, 3.8 Hz, 1H), 2.94 (s, 3H), 2.57 (dd, J=13.4, 11.1 Hz, 1H), 1.01 (s, 9H), 0.32 (d, J=6 Hz, 6H).

Workup

  1. customcould be detected on TLC (about 1.5 h)
  2. filtrationthen filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-109627482262450cbe8069a4bfb0b1d1
Source dataset
uspto-grants-2001_06
Patent number
US06242439B1

Reaction notes

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