tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate
• CAS No.: 194737-67-2
• Molecular Formula: C₃₂H₄₈N₂O₈SSi
• Molecular Weight: 648.893

Synonyms:tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate

Chemical Property:

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Technology Process of tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate

There total 8 articles about tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-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: 95.0%

methanesulfonyl chloride (124-63-0) + tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate (194737-66-1) → tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate (194737-67-2)

Guidance literature:

With triethylamine; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00261-9

Reference yield:

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one (134107-65-6) → tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate (194737-67-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / K₂CO₃, t-BuOOH / dimethylformamide; various solvent(s) / 0.5 h / Ambient temperature

2: BH₃*THF / tetrahydrofuran / 16 h / 0 °C

3: H₂ / 10percent Pd/C / ethyl acetate / 18 h / 3800 Torr

4: 73 percent / NaN₃, NH₄Cl / methanol; H₂O / 72 h / Heating

5: 59 percent / imidazole / dimethylformamide / 36 h / Ambient temperature

6: 96 percent / H₂ / 10percent Pd/C / methanol / 18 h / 3800 Torr

7: 95 percent / Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

With 1H-imidazole; tert.-butylhydroperoxide; sodium azide; borane-THF; hydrogen; potassium carbonate; ammonium chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(97)00261-9

Reference yield:

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (103201-79-2,1820583-17-2) → tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-mesyloxy-pyrrolidine-1-carboxylate (194737-67-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / PhSO₂Me, KH / tetrahydrofuran / 2 h / Ambient temperature

2: 87 percent / K₂CO₃, t-BuOOH / dimethylformamide; various solvent(s) / 0.5 h / Ambient temperature

3: BH₃*THF / tetrahydrofuran / 16 h / 0 °C

4: H₂ / 10percent Pd/C / ethyl acetate / 18 h / 3800 Torr

5: 73 percent / NaN₃, NH₄Cl / methanol; H₂O / 72 h / Heating

6: 59 percent / imidazole / dimethylformamide / 36 h / Ambient temperature

7: 96 percent / H₂ / 10percent Pd/C / methanol / 18 h / 3800 Torr

8: 95 percent / Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

With 1H-imidazole; tert.-butylhydroperoxide; sodium azide; borane-THF; methylphenylsulfonate; hydrogen; potassium hydride; potassium carbonate; ammonium chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(97)00261-9

upstream raw materials:

methanesulfonyl chloride

tert-butyl (2R,3S,4R)-4-tert-butoxycarboxamido-2-tert-butyldiphenylsilyloxymethyl-3-hydroxy-pyrrolidine-1-carboxylate

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

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