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Chemical Structure| 955400-17-6 Chemical Structure| 955400-17-6

Structure of 955400-17-6

Chemical Structure| 955400-17-6

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Product Details of [ 955400-17-6 ]

CAS No. :955400-17-6
Formula : C11H21NO3
M.W : 215.29
SMILES Code : O=C(N1C[C@H](COC)CC1)OC(C)(C)C
English Name :tert-Butyl (R)-3-(methoxymethyl)pyrrolidine-1-carboxylate
MDL No. :MFCD31734617

Safety of [ 955400-17-6 ]

Application In Synthesis of [ 955400-17-6 ]

* 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 [ 955400-17-6 ]

[ 955400-17-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 955400-17-6 ]
  • [ 955400-18-7 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride In water at 20℃;
70 mg With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; 2 Step 2: (R)-tert-butyl 3-(methoxymethyl)pyrrolidine-1 -carboxylate from Step 1 (100 mg, 0.46 mmol) in DCM (2 ml_) was mixed with 4M HCI in dioxane (2 ml_, 8.0 mmol) and the mixture stirred at RT for 2h. Volatiles were evaporated under reduced pressure, the residue co-evaporated to dryness with EtOAc and the product dried under vacuum to provide (R)-3- (methoxymethyl)pyrrolidine hydrochloride (70 mg) as an oil, that was used without further purification.
  • 2
  • [ 955400-18-7 ]
  • [ 138108-72-2 ]
  • [ 955400-17-6 ]
YieldReaction ConditionsOperation in experiment
65.4 % Stage #1: tert-butyl (R)-3-hydroxymethylpyrrolidine-1-carboxylate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Cooling with ice; Stage #2: (R)-3-(methoxymethyl)pyrrolidine hydrochloride In tetrahydrofuran; mineral oil at 20℃; 1 Preparation of (R)-3-(methoxymethyl)pyrrolidine hydrochloride: Step 1: (R)-tert- butyl 3-(hydroxymethyl)pyrrolidine-1 -carboxylate (1.00 g, 4.97 mmol) was dissolved in THF (20 ml_) and the solution cooled in an ice-water bath. NaH 60% oil dispersion (0.60 g, 14.91 mmol) was added portion wise and the reaction mixture was stirred at 0 °C for 15 min. lodomethane (1.55 ml_, 24 mmol) was slowly added and the reaction mixture was stirred overnight at RT. The reaction mixture was then quenched with sat. NH4CI solution and extracted with EtOAc (2 x 50 ml_). The organic layer was separated, dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated to dryness and purified by silica gel column chromatography (80 g) using EtOAc-hex 0 to 100%. (R)-tert-butyl 3-(methoxymethyl)pyrrolidine-1 -carboxylate (700 mg, 3.25 mmol, 65.4 % yield) was obtained as an colorless oil: 1H NMR (CDCl3) δ: 3.49 (dd, J = 11.0, 7.6 Hz, 1H), 3.43 (br s, 1H), 3.35 (s, 3H), 3.26 - 3.35 (m, 3H), 3.06 (dd, J = 10.7, 7.3 Hz, 1 H), 2.46 (spt, J = 7.3 Hz, 1 H), 1.91 - 2.02 (m, 1 H), 1.58 - 1.70 (m, 1 H), 1.46 (s, 9H).
65.4 % Stage #1: tert-butyl (R)-3-hydroxymethylpyrrolidine-1-carboxylate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Cooling with ice; Stage #2: (R)-3-(methoxymethyl)pyrrolidine hydrochloride In tetrahydrofuran; mineral oil at 20℃; 1 Preparation of (R)-3-(methoxymethyl)pyrrolidine hydrochloride: Step 1: (R)-tert- butyl 3-(hydroxymethyl)pyrrolidine-1 -carboxylate (1.00 g, 4.97 mmol) was dissolved in THF (20 ml_) and the solution cooled in an ice-water bath. NaH 60% oil dispersion (0.60 g, 14.91 mmol) was added portion wise and the reaction mixture was stirred at 0 °C for 15 min. lodomethane (1.55 ml_, 24 mmol) was slowly added and the reaction mixture was stirred overnight at RT. The reaction mixture was then quenched with sat. NH4CI solution and extracted with EtOAc (2 x 50 ml_). The organic layer was separated, dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated to dryness and purified by silica gel column chromatography (80 g) using EtOAc-hex 0 to 100%. (R)-tert-butyl 3-(methoxymethyl)pyrrolidine-1 -carboxylate (700 mg, 3.25 mmol, 65.4 % yield) was obtained as an colorless oil: 1H NMR (CDCl3) δ: 3.49 (dd, J = 11.0, 7.6 Hz, 1H), 3.43 (br s, 1H), 3.35 (s, 3H), 3.26 - 3.35 (m, 3H), 3.06 (dd, J = 10.7, 7.3 Hz, 1 H), 2.46 (spt, J = 7.3 Hz, 1 H), 1.91 - 2.02 (m, 1 H), 1.58 - 1.70 (m, 1 H), 1.46 (s, 9H).
 

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