Yohimban-16-carboxylicacid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16a,17b,18b,20a)- (9CI)

Base Information

Chemical Name:Yohimban-16-carboxylicacid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16a,17b,18b,20a)- (9CI)
CAS No.:6872-69-1
Molecular Formula:C₃₃H₄₀N₂O₉
Molecular Weight:608.689
Hs Code.:

Synonyms:3b,20a-Yohimban-16a-carboxylic acid, 18b-hydroxy-11,17b-dimethoxy-, methyl ester, 3,4,5-trimethoxybenzoate(ester) (8CI); Neoreserpine (7CI); Benz[g]indolo[2,3-a]quinolizine,yohimban-16-carboxylic acid deriv.; Neoreserpic acid, methyl ester,3,4,5-trimethoxybenzoate; Neoreserpin

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Chemical Property of Yohimban-16-carboxylicacid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16a,17b,18b,20a)- (9CI)

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Technology Process of Yohimban-16-carboxylicacid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16a,17b,18b,20a)- (9CI)

There total 71 articles about Yohimban-16-carboxylicacid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3b,16a,17b,18b,20a)- (9CI) 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: 95.0%

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 2901-66-8,16676-49-6,17138-18-0,20686-05-9,20686-09-3,101053-19-4
(+/-)-methyl reserpate

: 50-55-5,482-85-9,1263-58-7,6872-69-1,17138-19-1,17298-47-4,72151-85-0,72173-53-6,75331-15-6
(+/-)-3-isoreserpine

Guidance literature:: With pyridine; at 20 ℃; for 96h;
DOI:10.1021/ja055744x

Reference yield:

: 96648-91-8
(4aR^*,5S^*,6S^*,7R^*)-2-benzyl-3,4,4a,5,6,7-hexahydro-5-((methoxymethoxy)methyl)-6,7-oxy-1(2H)-isoquinolone

: 50-55-5,482-85-9,1263-58-7,6872-69-1,17138-19-1,17298-47-4,72151-85-0,72173-53-6,75331-15-6
(+/-)-3-isoreserpine

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / lithium 2-ethylhexanoate / 1,2-dimethoxy-ethane / 16 h / Heating

2: 98 percent / Ag₂O, CaSO₄ / 96 h / Ambient temperature

3: acid / methanol

4: pyridinium dichromate / dimethylformamide

6: alane

7: methanol / acid

8: 40 percent / hydrogen

9: 91 percent / 4-(dimethylamino)pyridine / pyridine; CH₂Cl₂ / 24 h / Ambient temperature

10: 93 percent / hydrogen / 20 percent Pd(OH)2/C / acetic acid / 24 h / 760 Torr

11: 69 percent / N,N-diisopropylethylamine, NaI / dimethylsulfoxide / 72 h / Ambient temperature

12: 1.) Hg(OAc)2, 2.) H₂S, 3.) Zn / 1.) aq. acetic acid, 85-90 deg C, 1.25 h, 2.) aq. acetic acid, 85-90 deg C to rt, 1 h, 3.) aq. HClO₄, THF, acetone, reflux, 15 min

With methanol; dmap; calcium sulfate; dipyridinium dichromate; hydrogen sulfide; mercury(II) diacetate; hydrogen; aluminium hydride; lithium 2-ethylhexanoate; N-ethyl-N,N-diisopropylamine; sodium iodide; silver(l) oxide; zinc; palladium dihydroxide; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja00254a036

Reference yield:

: 96648-91-8
(4aR^*,5S^*,6S^*,7R^*)-2-benzyl-3,4,4a,5,6,7-hexahydro-5-((methoxymethoxy)methyl)-6,7-oxy-1(2H)-isoquinolone

: 50-55-5,482-85-9,1263-58-7,6872-69-1,17138-19-1,17298-47-4,72151-85-0,72173-53-6,75331-15-6
(+/-)-reserpine

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / lithium 2-ethylhexanoate / 1,2-dimethoxy-ethane / 16 h / Heating

2: 98 percent / Ag₂O, CaSO₄ / 96 h / Ambient temperature

3: acid / methanol

4: pyridinium dichromate / dimethylformamide

6: alane

7: methanol / acid

8: 40 percent / hydrogen

9: 91 percent / 4-(dimethylamino)pyridine / pyridine; CH₂Cl₂ / 24 h / Ambient temperature

10: 93 percent / hydrogen / 20 percent Pd(OH)2/C / acetic acid / 24 h / 760 Torr

11: 69 percent / N,N-diisopropylethylamine, NaI / dimethylsulfoxide / 72 h / Ambient temperature

12: 1.) Hg(OAc)2, 2.) H₂S, 3.) Zn / 1.) aq. acetic acid, 85-90 deg C, 1.25 h, 2.) aq. acetic acid, 85-90 deg C to rt, 1 h, 3.) aq. HClO₄, THF, acetone, reflux, 15 min

With methanol; dmap; calcium sulfate; dipyridinium dichromate; hydrogen sulfide; mercury(II) diacetate; hydrogen; aluminium hydride; lithium 2-ethylhexanoate; N-ethyl-N,N-diisopropylamine; sodium iodide; silver(l) oxide; zinc; palladium dihydroxide; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja00254a036