(2RS₅S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one

Base Information

• Chemical Name: (2RS₅S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one
• CAS No.: 444753-24-6
• Molecular Formula: C₂₇H₃₅NO₆
• Molecular Weight: 469.578

Synonyms:(2RS₅S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one

Chemical Property of (2RS₅S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one

Chemical Property:

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Technology Process of (2RS₅S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one

There total 4 articles about (2RS₅S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one 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: 68.0%

butanone (78-93-3) + (5S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)morpholin-3-one (444753-23-5) → (2RS5S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one (444753-24-6)

Guidance literature:

(5S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)morpholin-3-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

butanone; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1135/cccc20020373

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2RS5S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one (444753-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 67 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: LHDMS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 68 percent / tetrahydrofuran / 2 h / -78 °C

With dmap; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1135/cccc20020373

Reference yield:

(S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol (85803-44-7) → (2RS5S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)-2-(RS)-2-(hydroxybutan-2-yl)-morpholin-3-one (444753-24-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: 51 percent / tetrahydrofuran / 3 h / Heating

2.1: 67 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

3.1: LHDMS / tetrahydrofuran / 0.5 h / -78 °C

3.2: 68 percent / tetrahydrofuran / 2 h / -78 °C

With dmap; sodium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1.2: Williamson reaction;

DOI:10.1135/cccc20020373

upstream raw materials:

butanone

(5S)-5-[4-(benzyloxy)benzyl]-4-(tert-butoxycarbonyl)morpholin-3-one

di-tert-butyl dicarbonate

(S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol

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