t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate

Base Information

• Chemical Name: t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate
• CAS No.: 147633-28-1
• Molecular Formula: C₁₅H₂₁F₂NO₃
• Molecular Weight: 301.333
• Mol file: 147633-28-1.mol

Synonyms:

Chemical Property of t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate

There total 10 articles about t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate 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:

benzylamine (100-46-9) → t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate (147633-28-1)

Guidance literature:

Multi-step reaction with 5 steps

2: 29 percent / activated Zn / tetrahydrofuran / 1 h / Heating

3: 86 percent / p-toluenesulfonic acid / methanol; H₂O / 2 h / 55 °C

4: 1.) chromium (VI) oxide, periodic acid, 2.) boron trifluoride etherate / 1.) acetone, water, 0 deg C, 20 min, 2.) CH₂Cl₂, cyclohexane, 0 deg C, 20 min

5: 1.) DIBAL (excess), 2.) NaBH₄ / 1.) Et₂O, -78 deg C, 30 min, 2.) EtOH, 0 deg C, 45 min

With chromium(VI) oxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; periodic acid; zinc; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4020(01)82003-2

Reference yield:

(S)-N-benzyl-2,3-O-isopropylidene-glyceraldimine (135821-68-0) → t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate (147633-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 29 percent / activated Zn / tetrahydrofuran / 1 h / Heating

2: 86 percent / p-toluenesulfonic acid / methanol; H₂O / 2 h / 55 °C

3: 1.) chromium (VI) oxide, periodic acid, 2.) boron trifluoride etherate / 1.) acetone, water, 0 deg C, 20 min, 2.) CH₂Cl₂, cyclohexane, 0 deg C, 20 min

4: 1.) DIBAL (excess), 2.) NaBH₄ / 1.) Et₂O, -78 deg C, 30 min, 2.) EtOH, 0 deg C, 45 min

With chromium(VI) oxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; periodic acid; zinc; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4020(01)82003-2

Reference yield:

(2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine (100777-91-1) → t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate (147633-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 13 percent / activated Zn / tetrahydrofuran / 1 h / Heating

2: 63 percent / p-toluenesulfonic acid / methanol; H₂O / 2.5 h / 55 °C

3: 1.) chromium (VI) oxide, periodic acid, 2.) boron trifluoride etherate / 1.) acetone, water, 0 deg C, 20 min, 2.) CH₂Cl₂, cyclohexane, 0 deg C, 20 min

4: 1.) DIBAL (excess), 2.) NaBH₄ / 1.) Et₂O, -78 deg C, 30 min, 2.) EtOH, 0 deg C, 45 min

With chromium(VI) oxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; periodic acid; zinc; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4020(01)82003-2

upstream raw materials:

(4R)-1-benzyl-4-(t-butyloxycarbonyl)-3,3-difluoroazetidin-2-one

(2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine

(S)-N-benzyl-2,3-O-isopropylidene-glyceraldimine

(4R)-1-benzyl-3,3-difluoro-4-<(1'R)-1',2'-dihydroxyethyl>azetidin-2-one

Refernces