Ethyl trifluoromethanesulphonate → HCID 131725727, compound

HRID 1823209Notes

Reaction equation

HRID 1823209 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:14][SiH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][CH2:10][C:9]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.O([CH2:51][CH3:52])S(C(F)(F)F)(=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:14][SiH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][C@@H:10]([CH2:51][CH3:52])[C:9]1=[O:32])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 67924Ethyl trifluoromethanesulphonateHCID 2733832Lithium HexamethyldisilazideHCID 131725728HCID 131725728, compound

Product 1

HCID 131725727HCID 131725727, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (5.0 g, 11.0 mmol) in THF (50 mL) at −78° C. was added LHMDS (1.0 M in THF, 12.6 mL, 12.6 mmol). The mixture was stirred for 30 min before ethyl triflate (1.78 mL, 1.25 equiv.) was added. The reaction was stirred between −78° C. to −40° C. for 45 min. It was quenched with 5% citric acid at −50° C., extracted with ethyl acetate. The combined organic phases were washed with 5% NaHCO3, brine, and dried over MgSO4NaHCO3, brine, and dried over MgSO4. Evaporation of the solvent and flash column chromatography (hexanes/EtOAc, 4:1) gave the desired product (90% yield) as viscous oil. 1HNMR (400 MHz, CDCl3) δ 7.63 (m, 4 H), 7.41 (m, 6 H), 4.13 (m, 2 H), 3.86 (m, 1 H), 3.74 (d, 1 H), 2.71 (m, 1 H), 2.24 (t, 1 H), 1.95 (m, 1 H), 1.78 (q, 1 H), 1.46 (s, 9 H), 0.95 (t, 3 H).

Workup

  1. additionwas added
  2. customIt was quenched with 5% citric acid at −50° C.
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with 5% NaHCO3, brine
  5. dry with materialdried over MgSO4NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent and flash column chromatography (hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-24d464183e0848b5bf1960a1f078b787
Source dataset
uspto-grants-2006_05
Patent number
US07037911B2

Reaction notes

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