(-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate

Base Information

Chemical Name:(-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate
CAS No.:935468-77-2
Molecular Formula:C₂₄H₃₀NO₅P
Molecular Weight:443.48
Hs Code.:

Synonyms:(-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate

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Chemical Property of (-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate

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Technology Process of (-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate

There total 6 articles about (-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

: 935468-76-1
(-)-(2R,5R,10S)-hexahydro-2-(2-hydroxyethyl)-5-methyl-1H-pyrrolizin-3-one

: 1623-08-1
phosphoric acid dibenzyl ester

: 935468-77-2
(-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate

Guidance literature:: With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1002/hlca.200790028

Reference yield:

: 878009-67-7
(+)-tert-butyl (4S)-2,2-dimethyl-4-[(E)-3-oxobut-1-en-1-yl]-1,3-oxazolidine-3-carboxylate

: 935468-77-2
(-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / H₂ / 10percent Pd/C / ethyl acetate / 21 h / 20 °C

2.1: TsOH; TFA / CH₂Cl₂ / 17 h / Heating

2.2: NaHB(OAc)3 / toluene / 12 h / Heating

2.3: 19 percent / K₂CO₃ / acetonitrile / 24 h / 20 °C

3.1: SO₃*Py / dimethylsulfoxide / 2.5 h / 5 °C

3.2: 55 percent / tetrahydrofuran / 22 h / 50 °C

4.1: 67 percent / H₂ / Pd/C / ethyl acetate / 14 h / 20 °C

5.1: TFA / CH₂Cl₂ / 1 h / 0 °C

5.2: 36 percent / DMAP / pyridine / 16 h / Heating

6.1: 86 percent / Ph₃P; Et₃N; DIAD / tetrahydrofuran / 3 h / 20 °C

With pyridine-SO₃ complex; di-isopropyl azodicarboxylate; hydrogen; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; 3.2: Wittig olefination / 6.1: Mitsunobu reaction;
DOI:10.1002/hlca.200790028

Reference yield:

: 878009-68-8
(+)-tert-butyl (4S)-2,2-dimethyl-4-(3-oxobutyl)-1,3-oxazolidine-3-carboxylate

: 935468-77-2
(-)-2-[(2R,5R,7aS)-hexahydro-5-methyl-3-oxo-1H-pyrrolizin-2-yl]ethyl bis(phenylmethyl) phosphate

Guidance literature:: Multi-step reaction with 5 steps

1.1: TsOH; TFA / CH₂Cl₂ / 17 h / Heating

1.2: NaHB(OAc)3 / toluene / 12 h / Heating

1.3: 19 percent / K₂CO₃ / acetonitrile / 24 h / 20 °C

2.1: SO₃*Py / dimethylsulfoxide / 2.5 h / 5 °C

2.2: 55 percent / tetrahydrofuran / 22 h / 50 °C

3.1: 67 percent / H₂ / Pd/C / ethyl acetate / 14 h / 20 °C

4.1: TFA / CH₂Cl₂ / 1 h / 0 °C

4.2: 36 percent / DMAP / pyridine / 16 h / Heating

5.1: 86 percent / Ph₃P; Et₃N; DIAD / tetrahydrofuran / 3 h / 20 °C

With pyridine-SO₃ complex; di-isopropyl azodicarboxylate; hydrogen; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; 2.2: Wittig olefination / 5.1: Mitsunobu reaction;
DOI:10.1002/hlca.200790028