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Structure of 23770-07-2

Chemical Structure| 23770-07-2

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Product Details of [ 23770-07-2 ]

CAS No. :23770-07-2
Formula : C12H15NO
M.W : 189.25
SMILES Code : O=C1CN(CC2=CC=CC=C2)C(C)C1
MDL No. :MFCD22369934
InChI Key :YKPHLMHWFYQKLQ-UHFFFAOYSA-N
Pubchem ID :18379325

Safety of [ 23770-07-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Application In Synthesis of [ 23770-07-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 23770-07-2 ]

[ 23770-07-2 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 23770-07-2 ]
  • [ 24424-99-5 ]
  • [ 362706-25-0 ]
YieldReaction ConditionsOperation in experiment
66.5% With hydrogen;palladium on carbon; In ethanol; under 2068.65 Torr; Step 5: terf-butyl 5-methyl-(pyrrolidin-3-one)-1-carboxylateA solution of <strong>[23770-07-2]1-benzyl-5-methylpyrrolidin-3-one</strong> (2 g, 10.57 mmol), BoC2O (2.77 g, 12.98 mmol) and Pd/C (0.3 g) in EtOH (20 mL) was stirred under H2 (40 psi) overnight. After TLC showed the reaction was complete, the reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (9:1 PE/EA) to give terf-butyl 5-methyl-(pyrrolidin-3-one)-1-carboxylate (1.4 g, 66.5%) as colorless oil (1.4 g, 66.5%): 1H NMR (400 MHz, CDCI3) delta ppm 7.33-7.23 (m, 5H), 4.18-4.15 (d, J = 13.2 Hz, 1 H), 3.29-3.14 (m, 1 H), 2.99-2.93 (m, 1 H), 2.65-2.60 (m, 1 H), 2.51-2.45 (m, 1 H), 2.16-2.08 (m, 1 H), 1.34-1.32 (m, 3H); ES-LCMS does not ionize.
54% With hydrogen; In ethyl acetate; (393e) Di tert-butyl dicarbonate (1.45 gm, 6.6 mmol) was added to a solution of <strong>[23770-07-2]1-benzyl-5-methyl-3-pyrrolidinone</strong> (1.13 gm, 6.0 mmol) in ethyl acetate (30 ml) and palladium hydroxide. The reaction was pressured to 50 psi hydrogen and shaken for 18 h. The reaction was filtered, concentrated and purified by flash chromatography to give N-Boc-5-methyl-3-pyrrolidinone (0.87 gm, 54%) as an oil. (393f) Following a procedure analogous to that used in example (357), but using the N-Boc-5-methyl-3-pyrrolidinone from step (393e) and triethyl phosphonoacetate in DMF with sodium hydride, to prepare the a-d unsaturated ester, the title compound (0.058 g. 44%) was prepared as a white amorphous solid, MS (M+H)+=494.
  • 3
  • ethyl 1-benzyl-2-methyl-4-oxo-3-pyrrolidinecarboxylate [ No CAS ]
  • [ 23770-07-2 ]
YieldReaction ConditionsOperation in experiment
46% With sulfuric acid; In water; (393d) A suspension of ethyl 1-benzyl-2-methyl-4-oxo-3-pyrrolidinecarboxylate (3.4 g, 13 mmol) in water (95 ml) and sulfuric acid (5 ml) was heated to 90 C. overnight. The mixture was allowed to cool was neutralized with sodium carbonate, extracted with methylene chloride. The combined organic layer filtered through a plug of silica gel and concentrated to give 1-benzyl-5-methyl-3-pyrrolidinone (1.13 gm, 46%) as a yellow oil, MS (M+H)+=190.
  • 4
  • [ 23770-07-2 ]
  • 1-benzyl-3-hydroxyimino-5-methylpyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium carbonate; In ethanol; (a) To 210 ml of aqueous solution containing 2.5 g of hydroxylamine hydrochloride was added 210 ml of ethanol solution containing 25 g of <strong>[23770-07-2]1-benzyl-5-methyl-3-pyrrolidone</strong> at about 15 C. 28 g of sodium carbonate was added, and the solution was stirred for 1 hour at the same tempereture. After the mixture was allowed to stand under ice-cooling overnight, 23 g of precipitated crude crystals of 1-benzyl-3-hydroxyimino-5-methylpyrrolidine having a melting point of 109-110 C. was obtained. Mass spectrum (m/e) 204 (M+)
  • 5
  • [ 23770-07-2 ]
  • (+/-)-trans-4-Acetylamino-1-benzyl-2-methylpyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 12 (+,-)-trans-4-Acetylamino-1-benzyl-2-methylpyrrolidine By reacting (+,-)-N-benzyl-5-methylpyrrolidin-3-one (prepared according to Prost et al., Helv. Chim Acta, 52:1134 (1969)) according to the procedures described in Examples 1f and 1g above, the title compound was obtained as a crystalline solid. MS M/Z: 233 (M+H). NMR (CDCl3) delta: 1.15 (d, 3H, J=6 Hz), 1.73 (m, 1H), 1.91 (s, 3H), 1.98 (m, 1H), 2.7-0 (sextet, 1H, J=6 Hz), 3.27 (m, 2H), 3.98 (d, 1H, J=13 Hz), 4.34 (m, 1H), 5.45 (br, 1H), 7.29 (m, 5H).
  • 6
  • methyl 1-benzyl-5-methyl-(pyrrolidin-3-one)-4-carboxylate [ No CAS ]
  • [ 23770-07-2 ]
YieldReaction ConditionsOperation in experiment
67% Step 4: 1-benzyl-5-methylpyrrolidin-3-oneB A solution of methyl 1-benzyl-5-methyl-(pyrrolidin-3-one)-4-carboxylate (44 g, 180.67 mmol) in H2SO4 (aq. 5%, 1600 ml.) was heated to reflux for 36 h. After LC-MS showed the reactant was completely consumed, the reaction mixture was cooled to room temperature. The mixture was neutralized with solid Na2CO3 to pH 8-9 and extracted with EtOAc (5 x 200 mL). The combined organic layers were dried and concentrated. The residue was purified by column chromatography (9:1 PE/EA) to give 1-benzyl-5- methylpyrrolidin-3-one as yellow oil (22 g, 67%): 1H NMR (400 MHz, CDCI3) delta ppm 7.33- 7.23 (m, 5H), 4.19-4.15 (d, J = 13.2 Hz, 1 H), 3.28-3.19 (m, 2H), 2.98-2.93 (m, 1 H), 2.65- 2.60 (m, 1 H), 2.51-2.49 (m, 1 H), 2.16-2.09 (m, 1 H), 1.34-1.32 (d, J = 6Hz, 3H); ES- LCMS m/z 190 {M+H)+
 

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