Chlorotrimethylsilane → HCID 60067078, compound

HRID 2308096Notes

Reaction equation

HRID 2308096 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:4].CCN(C(C)C)C(C)C.[Si:30](Cl)([CH3:33])([CH3:32])[CH3:31].CCOC(C)=O>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH2:7][N:6]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:4]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 60067078HCID 60067078, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolved (2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 1.5 g (5.37 mmol) in 10 mL of THF was treated with DIEA 1.31 mL (7.51 mmol) and 0.89 mL of TMS-Cl (6.98 mmol) added drop-wise while stirring. After 2 h of stirring, 50 mL of EtOAc was added and the mix was washed with Sat. NaHCO3 (3×50 mL). The organic layer was then dried over Na2SO4, filter through silica and concentrated to afford 1.84 g (97%) of (2S,4R)-4-Trimethylsilanyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester as a clear oil. HPLC: Rt 4.12 min. (100% area). 1H NMR (CDCl3, 400 MHz) δ: 7.37-7.28 (5H, m), 5.22-5.01 (2H, m), 4.51-4.41 (2H, m), 3.76 (2H, s), 3.70-3.66 (1H, m), 3.51-3.39.(1H, m), 2.22-2.16 (1H, m), 2.04 (3H, s), 0.11 (9H, s).

Workup

  1. additionadded drop-wise
  2. stirringAfter 2 h of stirring
  3. washthe mix was washed with Sat. NaHCO3 (3×50 mL)
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfilter through silica
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f8f0e2571d0040f19cadfaffda0cf157
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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