tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate

Base Information

• Chemical Name: tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate
• CAS No.: 784192-06-9
• Molecular Formula: C₂₀H₃₀N₂O₅
• Molecular Weight: 378.469

Synonyms:tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate

Chemical Property of tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate

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Technology Process of tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate

There total 2 articles about tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate 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: 73.0%

tert-butyl (2S)-2-((1R)-1-[(benzyloxy)carbonyl]amino-3-ethoxy-3-oxopropyl)tetrahydro-1H-1-pyrrolecarboxylate (784192-04-7) → tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate (784192-06-9)

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo048882y

Reference yield:

tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole (784191-98-6) → tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate (784192-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 73 percent / CaCl₂; NaBH₄ / tetrahydrofuran / 20 °C

With sodium tetrahydroborate; calcium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/jo048882y

Reference yield: 85.0%

tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate (784192-06-9) → benzyl N-(1S)-3-hydroxy-1-[(2R)-tetrahydro-1H-2-pyrrolyl]propylcarbamate (784192-07-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/jo048882y

upstream raw materials:

tert-butyl (2S)-2-((1R)-1-[(benzyloxy)carbonyl]amino-3-ethoxy-3-oxopropyl)tetrahydro-1H-1-pyrrolecarboxylate

tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole

Downstream raw materials:

benzyl N-(1S)-3-hydroxy-1-[(2R)-tetrahydro-1H-2-pyrrolyl]propylcarbamate

benzyl N-[(1S,7aR)-perhydro-1-pyrrolizinyl]carbamate

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