benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate

Base Information

Chemical Name:benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate
CAS No.:947595-52-0
Molecular Formula:C₁₈H₁₅Br₂N₃O₄
Molecular Weight:497.143
Hs Code.:

Synonyms:benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate

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Chemical Property of benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate

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Technology Process of benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate

There total 13 articles about benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate 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:

: 947595-51-9
C₁₈H₁₅N₃O₄Br₂

: 947595-52-0
benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 ℃; for 3h;
DOI:10.1021/ol0709735

Reference yield:

: 947595-45-1
benzyl {(1S,2E)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]pent-2-en-1-yl}carbamate

: 947595-52-0
benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 92 percent / Dowex 50W x8 / methanol / 26 h / Heating

2.1: 83 percent / (PCy₃)2Cl₂Ru=CHPh / benzene / 15 h / 60 °C

3.1: CSA / acetone / 6 h / 20 °C

3.2: 99 percent / H₂O; silica gel / CH₂Cl₂ / 7 h / 20 °C

4.1: CH₂Cl₂ / 0.5 h / 0 °C

5.1: 111 mg / aq. K₂CO₃ / methanol / 7 h / 20 °C

6.1: PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 0.67 h / -10 °C

6.2: 95 percent / CH₂Cl₂ / -10 - 20 °C

7.1: Zn; AcOH / tetrahydrofuran / 3 h / 20 °C

8.1: 221 mg / Na₂CO₃ / dimethylformamide / 15.5 h / 20 °C

9.1: 83 percent / Dowex 50W x8 / methanol / 6 h / Heating

10.1: IBX / dimethylsulfoxide / 8 h / 20 °C

11.1: 58 mg / i-Pr₂NEt / dimethylsulfoxide / 3 h / 20 °C

With carbon tetrabromide; Dowex 50W X₈; camphor-10-sulfonic acid; sodium carbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/ol0709735

Reference yield:

: 947595-38-2
benzyl {(1S,2E)-1-[(1S,2S)-1,2-dihydroxybut-3-en-1-yl]pent-2-en-1-yl}carbamate

: 947595-52-0
benzyl [(3S,3aS,9aR)-7,8-dibromo-2,3,3a,4,5,9a-hexahydro-1H-cyclopenta[e]pyrrolo[1,2-a]pyrazin-3-yl]carbamate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 83 percent / (PCy₃)2Cl₂Ru=CHPh / benzene / 15 h / 60 °C

2.1: CSA / acetone / 6 h / 20 °C

2.2: 99 percent / H₂O; silica gel / CH₂Cl₂ / 7 h / 20 °C

3.1: CH₂Cl₂ / 0.5 h / 0 °C

4.1: 111 mg / aq. K₂CO₃ / methanol / 7 h / 20 °C

5.1: PPh₃; CBr₄; Et₃N / CH₂Cl₂ / 0.67 h / -10 °C

5.2: 95 percent / CH₂Cl₂ / -10 - 20 °C

6.1: Zn; AcOH / tetrahydrofuran / 3 h / 20 °C

7.1: 221 mg / Na₂CO₃ / dimethylformamide / 15.5 h / 20 °C

8.1: 83 percent / Dowex 50W x8 / methanol / 6 h / Heating

9.1: IBX / dimethylsulfoxide / 8 h / 20 °C

10.1: 58 mg / i-Pr₂NEt / dimethylsulfoxide / 3 h / 20 °C

With carbon tetrabromide; Dowex 50W X₈; camphor-10-sulfonic acid; sodium carbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/ol0709735