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Chemical Structure| 146256-99-7 Chemical Structure| 146256-99-7
Chemical Structure| 146256-99-7

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Ethyl 1-Boc-4-hydroxypyrrolidine-3-carboxylate

CAS No.: 146256-99-7

4.5 *For Research Use Only !

Cat. No.: A366695 Purity: 98%

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Product Details of [ 146256-99-7 ]

CAS No. :146256-99-7
Formula : C12H21NO5
M.W : 259.30
SMILES Code : O=C(C1CN(C(OC(C)(C)C)=O)CC1O)OCC
MDL No. :MFCD24466305
InChI Key :JHBUFXKTKCCCKA-UHFFFAOYSA-N
Pubchem ID :53400859

Safety of [ 146256-99-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis [ 146256-99-7 ]

* 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 [ 146256-99-7 ]

[ 146256-99-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 146256-98-6 ]
  • [ 146256-99-7 ]
YieldReaction ConditionsOperation in experiment
98.9% With sodium tetrahydroborate; In methanol; at 10℃; for 0.833333h; 4.2.2 tert-Butyl 3-ethyl 4-hydroxypyrrolidine-1,3-dicarboxylate 2a To a suspension of NaBH4 (2.74 g, 72.3 mmol) in anhydrous methanol (290 mL) was added 1a (37.19 g, 144.6 mmol) at below 10 °C. The reaction mixture was stirred at the same temperature for 50 min, and then 20percent aqueous acetic acid was added dropwise to adjust pH 7.0 at 0 °C, and then concentrated under reduced pressure. The residue was dissolved with ethyl acetate (400 mL), and washed with water (50 mL * 3), brine (40 mL * 2), dried over anhydrous sodium sulfate, and evaporated under vacuo to afford the title compound 2a (37.11 g, 98.9percent) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) delta (ppm): 4.53-4.42 (m, 1H), 4.16-4.08 (m, 2H), 3.36-3.60 (m, 2H), 3.43 (brs, 1H), 3.28-3.25 (brs, 2H), 3.01-2.97 (brs, 1H), 1.42 (s, 9H), 1.28-1.21 (m, 3H). MS-ESI (m/z): 282.75 (M + Na)+.
With sodium cyanoborohydride; In methanol; b) 4-Hydroxy-pyrrolidine-1,3-dicarboxylic acid 1-tert.-butylester 3-ethylester To a solution of 5.15 g (20 mmol) 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert. butylester 3-ethylester in 30 ml methanol was added 1.88 g (30 mmol) sodium cyanoborohydride and a small amount of methylorange. With stirring the pH was adjusted to 3 by dropwise addition of 1N hydrochloric acid (color change from yellow to orange). After no more acid was consumed the mixture was stirred for one hour. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed twice with water, then with brine, dried over magnesium sulfate and evaporated. The residual yellow oil was used in the next step without any further purification. GC/MS (HP 5890 II/HP 5972; column: HP 5, 30 m*25 mm*0.25 mum film thickness, carrier gas: helium, temperature gradient: 50° C., 3 min; then with 20° C./min to 250° C.;) tR=12.44 min (no separation of diastereomers) m/z [percent]=259 (M+,0.3), 241 (0.7), 202(5), 186 (7), 158 (10), 112 (14), 68 (31), 57 (100).
With sodium cyanoborohydride; In methanol; b 4-Hydroxy-pyrrolidine-1,3-dicarboxylic acid 1-tert.-butylester 3-ethylester To a solution of 5.15 g (20 mmol) 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert. butylester 3-ethylester in 30 ml methanol was added 1.88 g (30 mmol) sodium cyanoborohydride and a small amount of methylorange. With stirring the pH was adjusted to 3 by dropwise addition of 1N hydrochloric acid (color change from yellow to orange). After no more acid was consumed the mixture was stirred for one hour. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed twice with water, then with brine, dried over magnesium sulfate and evaporated. The residual yellow oil was used in the next step without any further purification. GC/MS (HP 5890 II/HP 5972; column: HP 5,30 m*25 mm*0.25 (m film thickness, carrier gas: helium; temperature gradient: 50 ° C., 3 min; then with 20 ° C./min to 250 ° C.;) tR =12.44 min (no separation of diastereomers) m/z [percent]=259 (M+,0.3), 241 (0.7), 202 (5), 186 (7), 158 (10), 112 (14), 68 (31), 57 (100).
 

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