tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate

Base Information

• Chemical Name: tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate
• CAS No.: 1284207-03-9
• Molecular Formula: C₃₀H₃₉NO₄Si
• Molecular Weight: 505.729

Synonyms:tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate

Chemical Property of tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate

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Technology Process of tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate

There total 4 articles about tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-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: 49.0%

dicobalt octacarbonyl (15226-74-1,61091-28-9,61117-58-6) + tert-butyl N-[(1S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]-N-(but-2-yn-1-yl)carbamate (1284206-65-0) → tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (1284207-03-9)

Guidance literature:

dicobalt octacarbonyl; tert-butyl N-[(1S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]-N-(but-2-yn-1-yl)carbamate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

With trimethylamine-N-oxide; In dichloromethane; at -10 - 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201000706

Reference yield:

dicobalt octacarbonyl (15226-74-1,61091-28-9,61117-58-6) + tert-butyl N-[(1S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]-N-(but-2-yn-1-yl)carbamate (1284206-65-0) → tert-butyl (3S,3aR)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate + tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (1284207-03-9)

Guidance literature:

dicobalt octacarbonyl; tert-butyl N-[(1S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]-N-(but-2-yn-1-yl)carbamate; In dichloromethane; at 20 ℃; Inert atmosphere;

With trimethylamine-N-oxide; In dichloromethane; at -10 - 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201000706

Reference yield:

1,1-dimethylethyl [(1S)-1-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]carbamate (354153-37-0) → tert-butyl (3S,3aS)-3-{[(tert-butyldiphenylsilyl)oxy]methyl}-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (1284207-03-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 15-crown-5; sodium hydride / N,N-dimethyl-formamide / 5 h / -30 °C / Inert atmosphere

2.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

2.2: -10 - 20 °C / Inert atmosphere

With 15-crown-5; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; 2.1: Pauson-Khand reaction / 2.2: Pauson-Khand reaction;

DOI:10.1002/adsc.201000706

upstream raw materials:

dicobalt octacarbonyl

tert-butyl N-[(1S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]-N-(but-2-yn-1-yl)carbamate

1,1-dimethylethyl [(1S)-1-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)prop-2-en-1-yl]carbamate

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