(1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]

Base Information

Chemical Name:(1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]
CAS No.:726192-20-7
Molecular Formula:C₂₈H₃₅N₃O₄
Molecular Weight:477.604
Hs Code.:

Synonyms:(1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]

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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 (1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]

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Technology Process of (1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]

There total 1 articles about (1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline] 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: 44.0%

: 35132-20-8
(R,R)-1,2-diphenylethylenediamine

: (+/-)-7-tert-butoxycarbonyl-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one

: 726192-20-7
(1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]

: 727417-92-7
(1S,2S,3R,4R,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]

Guidance literature:: With 4 A molecular sieve; triethylamine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/jo049637h

Reference yield:

: 726192-20-7
(1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]

: 726192-23-0
[((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / H₃PO₄ / tetrahydrofuran / 0.5 h / 20 °C

2.1: 84 percent / Et₃N / dimethylformamide / 6 h / 60 °C

3.1: O₃ / CH₂Cl₂; methanol / 0.42 h / -78 °C

3.2: 89 percent / NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

4.1: 80 percent / PyBOP; diisopropylethylamine / dimethylformamide / 1 h

5.1: 78 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h

With phosphoric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049637h

Reference yield:

: 726192-20-7
(1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]

: 726192-32-1
(3aR,4S,6S,6aS)-4-(Benzyloxycarbonylmethyl-carbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / H₃PO₄ / tetrahydrofuran / 0.5 h / 20 °C

2.1: 84 percent / Et₃N / dimethylformamide / 6 h / 60 °C

3.1: O₃ / CH₂Cl₂; methanol / 0.42 h / -78 °C

3.2: 89 percent / NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

4.1: 80 percent / PyBOP; diisopropylethylamine / dimethylformamide / 1 h

With phosphoric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049637h