(-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate

Base Information

• Chemical Name: (-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate
• CAS No.: 929885-95-0
• Molecular Formula: C₂₂H₂₇NO₅
• Molecular Weight: 385.46

Synonyms:(-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate

Chemical Property of (-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate

Chemical Property:

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Technology Process of (-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate

There total 2 articles about (-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate 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%

(+)-tert-butyl (2S)-3-(1,3-benzodioxol-5-yl)-2-{(benzyl)[(tert-butoxy)carbonyl]amino}propanoate (929885-94-9) → (-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate (929885-95-0)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; ethanol; for 17h; Heating;

DOI:10.1002/hlca.200790006

Reference yield:

(2S,3R)-3-(1,3-benzodioxol-5-yl)-1-benzyl-aziridine-2-carboxylic acid tert-butyl ester (929885-93-8) → (-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate (929885-95-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / H₂ / Pd(OH)2/C / methanol / 6.5 h / 20 °C

2: 88 percent / LiBH₄ / tetrahydrofuran; ethanol / 17 h / Heating

With lithium borohydride; hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1002/hlca.200790006

Reference yield: 66.0%

(-)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(hydroxymethyl)ethyl]benzylcarbamate (929885-95-0) → (+)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(iodomethyl)ethyl]benzylcarbamate (929885-96-1)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/hlca.200790006

upstream raw materials:

(+)-tert-butyl (2S)-3-(1,3-benzodioxol-5-yl)-2-{(benzyl)[(tert-butoxy)carbonyl]amino}propanoate

(2S,3R)-3-(1,3-benzodioxol-5-yl)-1-benzyl-aziridine-2-carboxylic acid tert-butyl ester

Downstream raw materials:

(+)-tert-butyl [(1S)-2-(1,3-benzodioxol-5-yl)-1-(iodomethyl)ethyl]benzylcarbamate

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