3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester

Base Information

Chemical Name:3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester
CAS No.:138605-20-6
Molecular Formula:C₂₁H₃₀N₄O₃
Molecular Weight:386.494
Hs Code.:

Synonyms:3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester

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Chemical Property of 3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester

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Technology Process of 3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester

There total 12 articles about 3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester 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: 84.0%

: 138605-19-3
N-<4(S)-azido-5-oxo-5-<2-oxo-4(S)-(phenylmethyl)-3-oxazolidinyl>-3(R)-phenylpentyl>-L-norleucine 1,1-dimethylethyl ester

: 138605-20-6
3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester

Guidance literature:: In N,N-dimethyl-formamide; at 110 ℃; for 5h;
DOI:10.1021/jm00083a006

Reference yield:

: 4160-80-9
3-phenylglutaric acid anhydride

: 138605-20-6
3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 86 percent / NaBH₄ / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 0.5 h

2: 100 percent / 2.5 M aq. NaOH

3: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

4: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

5: TsOH / benzene / 2 h / 120 °C

6: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

7: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

8: 1.) potassium hexamethyldisilazide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide, acetic acid / 1.) toluene, THF, -78 deg C, 0.5 h, 2.) toluene, THF, from -78 deg C to 35 deg C, 0.5 h

9: 67 percent / acetic acid / tetrahydrofuran; H₂O / 6 h / Heating

10: 1.) 3A molecular sieves, 2.) NaCNBH₄ / 1.) MeOH, 0.5 h, 2.) MeOH, THF, RT, 3 h

11: 84 percent / dimethylformamide / 5 h / 110 °C

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; 3 A molecular sieve; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm00083a006

Reference yield:

: 61198-49-0,61949-75-5,71302-21-1,25547-53-9
4-phenyltetrahydropyran-2-one

: 138605-20-6
3(S)-azido-α(S)-butyl-2-oxo-4(R)-phenyl-1-piperidineacetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / 2.5 M aq. NaOH

2: 57 percent / hexamethylphosphoric acid triamide; ethanol / Ambient temperature

3: 1.) oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, DMSO, -78 deg C, 0.5 h, 2.) CH₂Cl₂, DMSO, from -78 deg C to RT

4: TsOH / benzene / 2 h / 120 °C

5: 93 percent / 1 M aq. NaOH / tetrahydrofuran / 10 h / Heating

6: 1.) pivaloyl chloride, Et₃N / 1.) THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 40 min

7: 1.) potassium hexamethyldisilazide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide, acetic acid / 1.) toluene, THF, -78 deg C, 0.5 h, 2.) toluene, THF, from -78 deg C to 35 deg C, 0.5 h

8: 67 percent / acetic acid / tetrahydrofuran; H₂O / 6 h / Heating

9: 1.) 3A molecular sieves, 2.) NaCNBH₄ / 1.) MeOH, 0.5 h, 2.) MeOH, THF, RT, 3 h

10: 84 percent / dimethylformamide / 5 h / 110 °C

With sodium hydroxide; oxalyl dichloride; 3 A molecular sieve; 2,4,6-Triisopropylbenzenesulfonyl azide; pivaloyl chloride; potassium hexamethylsilazane; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm00083a006