(S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate

Base Information

• Chemical Name: (S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate
• CAS No.: 865172-71-0
• Molecular Formula: C₂₆H₂₃BrN₂O₅
• Molecular Weight: 523.383

Synonyms:(S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate

Chemical Property of (S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate

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Technology Process of (S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate

There total 2 articles about (S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-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: 75.0%

(5-bromo-2,3-dihydro-1H-inden-1-ylidene)methyl methyl ether (701232-87-3) + dibenzyl azodicarboxylate (2449-05-0) → (S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate (865172-71-0)

Guidance literature:

With D-Prolin; In acetonitrile; for 4h;

DOI:10.1021/ol0512942

Reference yield:

5-Bromo-1-indanone (34598-49-7) → (S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate (865172-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / tBuOK / tetrahydrofuran / -20 - 20 °C

2: 75 percent / (R)-proline / acetonitrile / 4 h

With potassium tert-butylate; D-Prolin; In tetrahydrofuran; acetonitrile; 1: Wittig olefination;

DOI:10.1021/ol0512942

Reference yield: 81.0%

(S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate (865172-71-0) + diazomethyl-trimethyl-silane (18107-18-1) → C27H25BrN2O6 (865172-72-1)

Guidance literature:

(S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate; With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 4 ℃; for 12h;

diazomethyl-trimethyl-silane; In methanol; diethyl ether; toluene;

DOI:10.1021/ol0512942

upstream raw materials:

(5-bromo-2,3-dihydro-1H-inden-1-ylidene)methyl methyl ether

dibenzyl azodicarboxylate

5-Bromo-1-indanone

Downstream raw materials:

C₂₇H₂₅BrN₂O₆

C₃₁H₃₅N₂O₉P

(S)-1-amino-5-phosphonoindan-1-carboxylic acid

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