(3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]

Base Information

Chemical Name:(3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]
CAS No.:479064-40-9
Molecular Formula:C₃₂H₄₅NO₅Si
Molecular Weight:551.798
Hs Code.:

Synonyms:(3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]

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Technology Process of (3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]

There total 16 articles about (3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane] 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: 87.0%

: 107-21-1
ethylene glycol

: 479064-39-6
tert-butyl (3R)-3-tert-butyldiphenylsilyloxy-8-oxo-1-azaspiro[4.5]decane-1-carboxylate

: 479064-40-9
(3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]

Guidance literature:: With toluene-4-sulfonic acid; In benzene; for 3h; Heating;
DOI:10.1016/S0040-4020(02)01292-9

Reference yield:

: 226225-42-9
(2S,4R)-N-tert-butyloxycarbonyl-4-[(tert-butyldiphenylsilyl)oxy]pyrrolidine-2-carboxylic acid methyl ester

: 479064-40-9
(3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]

Guidance literature:: Multi-step reaction with 9 steps

1: 15 percent / LDA; HMPA / tetrahydrofuran / -78 °C

2: 90 percent / DIBAH / toluene / -30 °C

3: 81 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

4: 80 percent / CuCl; PdCl₂; oxygen / dimethylformamide; H₂O / 20 °C

5: 96 percent / KOH / ethanol / 0 °C

6: Et₃N / CH₂Cl₂ / 0 - 20 °C

7: silica gel / hexane; ethyl acetate

8: 73 percent / H₂ / 10 percent Pd(OH)2/C / benzene

9: 87 percent / TsOH*H₂O / benzene / 3 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; oxygen; silica gel; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 4: Wacker oxidation;
DOI:10.1016/S0040-4020(02)01292-9

Reference yield:

: 479064-47-6
2-but-3-enyl-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 479064-40-9
(3R)-dispiro[1-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / DIBAH / toluene / -30 °C

2: 81 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

3: 80 percent / CuCl; PdCl₂; oxygen / dimethylformamide; H₂O / 20 °C

4: 96 percent / KOH / ethanol / 0 °C

5: Et₃N / CH₂Cl₂ / 0 - 20 °C

6: silica gel / hexane; ethyl acetate

7: 73 percent / H₂ / 10 percent Pd(OH)2/C / benzene

8: 87 percent / TsOH*H₂O / benzene / 3 h / Heating

With potassium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; oxygen; silica gel; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; copper(l) chloride; palladium dichloride; palladium dihydroxide; In ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 3: Wacker oxidation;
DOI:10.1016/S0040-4020(02)01292-9