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126424-76-8

126424-76-8

Identification

Synonyms:3H-Pyrrolizin-3-one,5,6,7,7a-tetrahydro-, (R)-; (-)-Pyrrolam A; (R)-(-)-Pyrrolam A; (R)-Pyrrolam A;Pyrrolam A

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

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  • Manufacture/Brand:AccelPharmtech
  • Product Description:(7aR)-5,6,7,7a-tetrahydro-3H-Pyrrolizin-3-one 97.00%
  • Packaging:5G
  • Price:$ 3900
  • Delivery:In stock
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  • Manufacture/Brand:AccelPharmtech
  • Product Description:(7aR)-5,6,7,7a-tetrahydro-3H-Pyrrolizin-3-one 97.00%
  • Packaging:1G
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Relevant articles and documentsAll total 9 Articles be found

An efficient route to the pyrrolizidine ring system via an N-acyl anion cyclisation process

Murray, Anthony,Proctor, George R.,Murray, P. John

, p. 3757 - 3766 (1996)

An enantioselective route to the pyrrolizidine ring system has been developed which uses an N-acyl anion cyclisation reaction as the key step. This methodology has provided the natural pyrrolizidines (-)-(1R, 8S)-1-hydroxy-pyrrolizidine 7, (-)-pyrrolizidin-1-ene-3-one 9 and (±)-trachelanthamidine 14. Extension of the process to an N-propionyl substrate provides ready access to a series of 2-methyl pyrrolizidines.

Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: Synthesis of (R)-pyrrolam A

Marsh, Barrie J.,Adams, Harry,Barker, Mike D.,Kutama, Ibrahim U.,Jones, Simon

supporting information, p. 3780 - 3783 (2014/08/05)

A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.

Enantioselective synthesis of condensed and transannular ring skeletons containing pyrrolidine moiety

Mo, Fanyang,Li, Fei,Qiu, Di,Wang, Jianbo

experimental part, p. 1274 - 1279 (2010/03/30)

A new approach toward condensed and transannular ring structures containing pyrrolidine unit has been developed, based on diastereoselective nucleophilic addition of lithium enolate of α-diazoacetoacetate to chiral N-sulfinyl imine and ring-closing metathesis.

Synthesis of (-)-(R)-pyrrolam A and studies on its stability: A caveat on computational methods

Watson, Rhett T.,Gore, Vinayak K.,Chandupatla, Kishan R.,Dieter, R. Karl,Snyder, James P.

, p. 6105 - 6114 (2007/10/03)

The asymmetric synthesis of (-)-(R)-pyrrolam A was achieved in three operations from N-Boc pyrrolidine via α-(N-carbamoyl)alkylcuprate vinylation reaction followed by N-Boc deprotection and cyclization. One-pot deprotection-cyclization procedures led to mixtures of pyrrolam A and its double bond isomers. These isomerization events could be circumvented by use of a two-step procedure. To guide aspects of the experiments, a series of computational energy evaluations and chemical shift predictions were performed with molecular mechanics, semiempirical, ab initio, and density functional methods. The relative stabilities of the double bond isomers, as estimated by experiment, challenged a number of computational methods, and only the MP2 model with its moderate degree of electron correlation came close to matching the experimental data. The MP2 method was further applied to an unusual aspect of the double bond migration between pyrrolam A and its isomer 9. The reaction (1 to 9) on neat samples is irreversible without racemization, and the alumina-mediated equilibration is accompanied by complete loss of enantiomeric excess. The source of the irreversibility was traced to asymmetric charge distribution in the intermediate dienolate anion. The analysis ultimately led to a semiquantitative sketch of the pyrrolam energy surface.

Process route upstream and downstream products

Process route

(R)-1-(2-vinylpyrrolidin-1-yl)prop-2-en-1-one

(R)-1-(2-vinylpyrrolidin-1-yl)prop-2-en-1-one

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 80 ℃; Inert atmosphere;
68%
C<sub>21</sub>H<sub>25</sub>NO<sub>7</sub>S<sub>2</sub>
254730-12-6

C21H25NO7S2

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
With sodium hydride; In tetrahydrofuran; at -10 - 0 ℃; for 3.5h;
83.5%
ethyl 3-[2(R)-2-pyrrolidinyl]-2-(Z)-propenoate hydrochloride

ethyl 3-[2(R)-2-pyrrolidinyl]-2-(Z)-propenoate hydrochloride

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
With sodium hydrogencarbonate; In dichloromethane; water;
91%
C<sub>21</sub>H<sub>19</sub>NO

C21H19NO

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
at 226 - 490 ℃; for 0.5h; under 0.00750075 Torr; Pyrolysis;
69%
(R)-1-aza-2-oxobicyclo<3.3.0>oct-3-enyl trifluoromethanesulfonate
173290-27-2

(R)-1-aza-2-oxobicyclo<3.3.0>oct-3-enyl trifluoromethanesulfonate

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); tri-n-butyl-tin hydride; lithium chloride; In tetrahydrofuran; for 2h; Heating;
83%
(R)-1-benzyloxypyrrolizidin-1-en-3-one
945917-63-5

(R)-1-benzyloxypyrrolizidin-1-en-3-one

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: hydrogen / Pd on charcoal / methanol / 2 h / 20 °C / 760.05 Torr
2: NaBH4 / CH2Cl2; acetic acid / 1 h / 0 °C
3: 90 percent / triethylamine / CH2Cl2 / 18 h / 0 - 20 °C
4: triethylamine / CH2Cl2 / 18 h / Heating
With sodium tetrahydroborate; hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; acetic acid;
C<sub>13</sub>H<sub>15</sub>NOSe

C13H15NOSe

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
With dihydrogen peroxide; In tetrahydrofuran; at 0 ℃;
(3R,3aS,9aR)-2,3,3a,4,9,9a-hexahydro-3-allyl-2-(p-methoxyphenyl)-4,9-[1',2']benzeno-1H-benz[f]isoindol-1-one

(3R,3aS,9aR)-2,3,3a,4,9,9a-hexahydro-3-allyl-2-(p-methoxyphenyl)-4,9-[1',2']benzeno-1H-benz[f]isoindol-1-one

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: ammonium cerium (IV) nitrate / acetonitrile; water / 0.55 h / 0 °C
2.1: borane-THF / tetrahydrofuran / 1 h / 0 - 20 °C
2.2: 1 h
3.1: triethylamine / dichloromethane / 0.17 h / -10 °C
3.2: 1 h / -10 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 24 h / Reflux
5.1: 0.5 h / 226 - 490 °C / 0.01 Torr / Pyrolysis
With ammonium cerium (IV) nitrate; borane-THF; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
(3R,3aS,9aR)-2,3,3a,4,9,9a-hexahydro-3-allyl-4,9-[1',2']benzeno-1H-benz[f]isoindol-1-one

(3R,3aS,9aR)-2,3,3a,4,9,9a-hexahydro-3-allyl-4,9-[1',2']benzeno-1H-benz[f]isoindol-1-one

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: borane-THF / tetrahydrofuran / 1 h / 0 - 20 °C
1.2: 1 h
2.1: triethylamine / dichloromethane / 0.17 h / -10 °C
2.2: 1 h / -10 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 24 h / Reflux
4.1: 0.5 h / 226 - 490 °C / 0.01 Torr / Pyrolysis
With borane-THF; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; ethanol; dichloromethane;
(3R,3aS,9aR)-2,3,3a,4,9,9a-hexahydro-3-(3-hydroxypropyl)-4,9-[1',2']benzeno-1H-benz[f]isoindol-1-one

(3R,3aS,9aR)-2,3,3a,4,9,9a-hexahydro-3-(3-hydroxypropyl)-4,9-[1',2']benzeno-1H-benz[f]isoindol-1-one

pyrrolam A
126424-76-8

pyrrolam A

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 0.17 h / -10 °C
1.2: 1 h / -10 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 24 h / Reflux
3.1: 0.5 h / 226 - 490 °C / 0.01 Torr / Pyrolysis
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In ethanol; dichloromethane;

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