trans-tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

Base Information

• Chemical Name: trans-tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate
• CAS No.: 1174020-43-9
• Molecular Formula: C₁₀H₁₈FNO₃
• Molecular Weight: 219.256
• Mol file: 1174020-43-9.mol

Synonyms:trans-tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate;(3R,4R)-tert-Butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

Chemical Property of trans-tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

Chemical Property:

• Boiling Point: 300.8±42.0 °C(Predicted)
• PKA: 13.65±0.40(Predicted)
• PSA: 49.77000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 1.26410
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99%, ^*data from raw suppliers

(3R,4R)-1-Boc-3-fluoro-4-hydroxypiperidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of trans-tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

There total 4 articles about trans-tert-butyl 3-fluoro-4-hydroxypiperidine-1-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:

(anti)-3-fluoro-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (955029-44-4) → tert-butyl (3S,4S)-3-fluoro-4-hydroxypiperidine-1-carboxylate (1174020-44-0,955029-44-4) + tert-butyl (3R,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate (1174020-43-9,955029-44-4)

Guidance literature:

With Chiralpak AD-H; In methanol; Resolution of racemate;

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl (3S,4S)-3-fluoro-4-hydroxypiperidine-1-carboxylate (1174020-44-0,955029-44-4) + tert-butyl (3R,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate (1174020-43-9,955029-44-4)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / N,N-dimethyl-formamide / 80 °C

2: Selectfluor / acetonitrile / 1.5 h / 20 °C

3: methanol; sodium tetrahydroborate / 2 h

4: Chiralpak AD-H / methanol / Resolution of racemate

With methanol; sodium tetrahydroborate; Selectfluor; triethylamine; In methanol; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate (211108-50-8) → tert-butyl (3S,4S)-3-fluoro-4-hydroxypiperidine-1-carboxylate (1174020-44-0,955029-44-4) + tert-butyl (3R,4R)-3-fluoro-4-hydroxypiperidine-1-carboxylate (1174020-43-9,955029-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; sodium tetrahydroborate / 2 h

2: Chiralpak AD-H / methanol / Resolution of racemate

With methanol; sodium tetrahydroborate; In methanol;

upstream raw materials:

(anti)-3-fluoro-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

N-tert-butyloxycarbonylpiperidin-4-one

tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate

tert-butyl 4-[(trimethylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate

Downstream raw materials:

2-(((3R,4R)-3-fluoro-1-(2-(4-(trifluoromethoxy)phenyl)acetyl)piperidin-4-yl)oxy)-4-(2-hydroxy-2-methylpropoxy)benzamide

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