2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate

Base Information

Chemical Name:2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate
CAS No.:480460-75-1
Molecular Formula:C₁₈H₂₃NO₆
Molecular Weight:349.384
Hs Code.:

Synonyms:2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate

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Chemical Property of 2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate

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Technology Process of 2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate

There total 4 articles about 2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate 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%

: 176436-12-7
2-benzyl 1-tert-butyl (2S)-6-oxo-1,2-piperidinedicarboxylate

: 480460-75-1
2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate

Guidance literature:: 2-benzyl 1-tert-butyl (2S)-6-oxo-1,2-piperidinedicarboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2.5h;

With (+)-(10-camphorsulfonyl)oxaziridine; In tetrahydrofuran; at -78 ℃; for 16h; Further stages.;
DOI:10.1021/jo025950c

Reference yield:

: 30925-18-9
2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

: 480460-75-1
2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: EDC; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: 6.34 g / NaBH₄; AcOH / CH₂Cl₂ / 48 h / 20 °C

3.1: 75 percent / toluene / Heating

4.1: LiHMDS / tetrahydrofuran / 2.5 h / -78 °C

4.2: 88 percent / (+)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran / 16 h / -78 °C

With dmap; sodium tetrahydroborate; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo025950c

Reference yield:

: 480460-68-2
benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-(2,2-dimethyl-4,6-dioxo-1,3-dioxolan-5-yl)butanoate

: 480460-75-1
2-benzyl 1-tert-butyl (2S,5R)-5-hydroxy-6-oxo-1,2-piperidinedicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 75 percent / toluene / Heating

2.1: LiHMDS / tetrahydrofuran / 2.5 h / -78 °C

2.2: 88 percent / (+)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran / 16 h / -78 °C

With lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1021/jo025950c