1-Penten-3-one → Ethyl 3-hydroxy-3-methyl-1-tosylpyrrolidine-2-carboxylate

HRID 1724788Notes

Reaction equation

HRID 1724788 reaction equation
N12CCCN=C1CCCCC2.[CH:12]([C:14]([CH2:16]C)=[O:15])=[CH2:13].[CH2:18]([O:20][C:21](=[O:34])[CH2:22][NH:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH3:19]>C1COCC1.CCOCC>[CH2:18]([O:20][C:21]([CH:22]1[C:14]([OH:15])([CH3:16])[CH2:12][CH2:13][N:23]1[S:24]([C:27]1[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=1)(=[O:25])=[O:26])=[O:34])[CH3:19]

Participants

6

Reactant 3

HCID 153941-Penten-3-oneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 230685Ethyl 2-(4-methylphenylsulfonamido)acetate

Product 1

HCID 15747129Ethyl 3-hydroxy-3-methyl-1-tosylpyrrolidine-2-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) (7 mL, 47.08 mmol) was added to a stirred solution of ethyl vinyl ketone (1.75 mL, 21.4 mmol) and ethyl N-p-toluenesulfonylglycinate 81 (5.5 g, 21.4 mL) in THF (50 mL). The resulting mixture was stirred overnight at room temperature. The mixture was diluted with ether, washed with 5% aq. HCl, 5% sodium bicarbonate solution and water. The combined organics were dried with Na2SO4, filtered, evaporated under reduced pressure to give crude 82 (5.3 g, 76%) as a yellow oil (diastereoisomers mixture). 1H-NMR (400 MHz, CDCl3): δ 1.29 (m, 6H), 1.75 (m, 1H), 2.09 (m, 1H), 2.43 (s, 3H), 3.40 (m, 1H), 3.56 (m, 1H), 4.04 (s, 1H), 4.20 (m, 2H), 7.30 (d, 2H), 7.75 (d, 2H) ppm. 13C-NMR (100 MHz, CDCl3): δ 14.12, 15.28, 23.04, 25.60, 26.27, 38.20, 38.86, 46.26, 46.46, 61.49, 61.65, 69.10, 71.69, 127.51, 129.70, 134.83, 134.91, 143.58, 143.84, 170.03, 170.45 ppm. DEPT (100 MHz, CDCl3): CH3 carbons: 14.12, 15.28, 23.04, 25.60, 26.27; CH2 carbons: 38.20, 38.86, 46.26, 46.46, 61.49, 61.65; CH carbons: 69.10, 71.69, 127.51, 129.70 ppm.

Workup

  1. washwashed with 5% aq. HCl, 5% sodium bicarbonate solution and water
  2. dry with materialThe combined organics were dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1c5d5b25b3d54a4aa1172ad12c9d8258
Source dataset
uspto-grants-2009_02
Patent number
US07488747B2

Reaction notes

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