methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate

Base Information

Chemical Name:methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate
CAS No.:157425-67-7
Molecular Formula:C₂₁H₁₈N₂O₅
Molecular Weight:378.384
Hs Code.:

Synonyms:methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate

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Chemical Property of methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate

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Technology Process of methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate

There total 14 articles about methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate 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: 88.0%

: 157425-66-6
4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

: 157425-67-7
methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate

Guidance literature:: With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; a) 0 deg C, 10 min, b) 26 deg C, 4 h;
DOI:10.1248/cpb.44.67

Reference yield:

: trans-(+/-)-5-benzyloxy-1-(benzyloxycarbonyl)-2-<2-<3-bromo-5-(methoxycarbonyl)-1H-pyrrol-2-yl>-2-oxoethyl>-1,2,5,6-tetrahydropyridine

: 157425-67-7
methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 11 percent / Pd(OAc)2, (o-tol)3P, Et₃N / acetonitrile / 26 h / 110 °C

2: 76 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / a) -20 deg C, 2 h, b) 0 deg C, 1.5 h

3: Et₃N / CH₂Cl₂ / a) 0 deg C, 10 min, b) 22 deg C, 1.5 h

4: 1 N Bu₄NF / tetrahydrofuran / 13 h / 0 - 22 °C

5: 21 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 - -10 °C

6: 24 mg / p-TsOH*H₂O / acetone / 2.5 h / 24 °C

7: 79 percent / NaBH₄ / methanol / 0.33 h / -20 °C

8: 88 percent / 1,1'-(azodicarbonyl)dipiperidine, Bu₃P / tetrahydrofuran / a) 0 deg C, 10 min, b) 26 deg C, 4 h

With palladium diacetate; sodium tetrahydroborate; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; tris-(o-tolyl)phosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; methanol; dichloromethane; acetone; acetonitrile;
DOI:10.1248/cpb.44.67

Reference yield:

: trans-(+/-)-5-acetoxy-1-(benzyloxycarbonyl)-2-<2-<3-bromo-5-(methoxycarbonyl)-1H-pyrrol-2-yl>-2-oxoethyl>-1,2,5,6-tetrahydro-5-hydroxypyridine

: 157425-67-7
methyl (+/-)-2-(benzyloxycarbonyl)-1,2,4,5,8,8a-hexahydro-4-oxacyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / 1.5 percent K₂CO₃ / methanol / 2 h / 19 °C

2: 72 percent / trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / a) 0 deg C, 20 min, b) 20 deg C, 3 h

3: 11 percent / Pd(OAc)2, (o-tol)3P, Et₃N / acetonitrile / 26 h / 110 °C

4: 76 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / a) -20 deg C, 2 h, b) 0 deg C, 1.5 h

5: Et₃N / CH₂Cl₂ / a) 0 deg C, 10 min, b) 22 deg C, 1.5 h

6: 1 N Bu₄NF / tetrahydrofuran / 13 h / 0 - 22 °C

7: 21 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 - -10 °C

8: 24 mg / p-TsOH*H₂O / acetone / 2.5 h / 24 °C

9: 79 percent / NaBH₄ / methanol / 0.33 h / -20 °C

10: 88 percent / 1,1'-(azodicarbonyl)dipiperidine, Bu₃P / tetrahydrofuran / a) 0 deg C, 10 min, b) 26 deg C, 4 h

With palladium diacetate; sodium tetrahydroborate; tributylphosphine; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; tris-(o-tolyl)phosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetone; acetonitrile;
DOI:10.1248/cpb.44.67