(2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one

Base Information

Chemical Name:(2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one
CAS No.:132143-01-2
Molecular Formula:C₂₈H₃₄N₂O₄
Molecular Weight:462.589
Hs Code.:

Synonyms:(2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one

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Chemical Property of (2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one

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Technology Process of (2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one

There total 14 articles about (2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one 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: 69.0%

: 132143-13-6
(2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-2'-ethoxy-1'-((Z)-6-trimethylsilanyl-hex-4-enyl)-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one

: 132143-00-1
C₂₈H₃₂N₂O₃

: 132143-01-2
(2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one

Guidance literature:: With calcium hydride; boron trifluoride diethyl etherate; In dichloromethane; for 60h; Ambient temperature;
DOI:10.1016/S0040-4020(01)90540-X

Reference yield:

: 58594-50-6
3-(2'-nitrophenyl)pyrrolidine-2,5-dione

: 132143-01-2
(2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N / DMAP / CH₂Cl₂ / 0 deg C to room temperature

2: 95 percent / H₂ / 10percent Pd/C / toluene; ethanol / 18 h / 760 Torr

3: toluene / Ambient temperature

4: 1.5 M n-BuLi / 2-methyl-propan-2-ol; tetrahydrofuran; hexane; toluene / 0.5 h / 5 °C

5: toluene

6: 20percent aq. HCl / ethanol / Ambient temperature

7: 98 percent / dimethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / Ambient temperature

8: 54 percent / NaBH₄, 2 N H₂SO₄ / ethanol / 0 °C

9: 1.) Et₃N, MeSO₂Cl / 1.) THF, -30 deg C to room temperature, 15 min, 2.) 90 min

10: 26 percent / BF₃*Et₂O, CaH₂ / CH₂Cl₂ / 60 h

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; calcium hydride; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; methanesulfonyl chloride; dimethyl azodicarboxylate; triethylamine; triphenylphosphine; dmap; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)90540-X

Reference yield:

: 132143-08-9
1-(tert-Butyl-dimethyl-silanyl)-3-(2-nitro-phenyl)-pyrrolidine-2,5-dione

: 132143-01-2
(2R,3'R)-1-Acetyl-2-(2-benzyloxy-ethyl)-1'-hex-5-enyl-2'-hydroxy-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-5'-one

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / H₂ / 10percent Pd/C / toluene; ethanol / 18 h / 760 Torr

2: toluene / Ambient temperature

3: 1.5 M n-BuLi / 2-methyl-propan-2-ol; tetrahydrofuran; hexane; toluene / 0.5 h / 5 °C

4: toluene

5: 20percent aq. HCl / ethanol / Ambient temperature

6: 98 percent / dimethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / Ambient temperature

7: 54 percent / NaBH₄, 2 N H₂SO₄ / ethanol / 0 °C

8: 1.) Et₃N, MeSO₂Cl / 1.) THF, -30 deg C to room temperature, 15 min, 2.) 90 min

9: 26 percent / BF₃*Et₂O, CaH₂ / CH₂Cl₂ / 60 h

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; calcium hydride; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; methanesulfonyl chloride; dimethyl azodicarboxylate; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)90540-X