1-(Tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: 1-(Tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS No.: 59433-50-0
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• European Community (EC) Number: 854-296-9
• NSC Number: 334360,164660,108689
• Nikkaji Number: J2.540.441F
• ChEMBL ID: CHEMBL1702785
• Mol file: 59433-50-0.mol

Synonyms:59433-50-0;Boc-DL-Pro-OH;1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;N-Boc-DL-proline;1-(tert-Butoxycarbonyl)proline;BOC-DL-Proline;1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid;Pyrrolidine-1,2-Dicarboxylic Acid 1-Tert-Butyl Ester;MFCD00520915;N-(TERT-BUTOXYCARBONYL)PYRROLIDINE-2-CARBOXYLIC ACID;tert-Butoxycarbonylproline;MFCD00037324;MFCD00063226;Cambridge id 5211805;SCHEMBL67045;91716-96-0;MLS000060917;N-t-butoxycarbonyl-DL-proline;1, 1-tert-butyl ester, L-;(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;CHEMBL1702785;1-(tert-Butoxycarbonyl)proline #;HMS1609D11;HMS2397P09;HMS3343H11;N-Boc-pyrolidin-2-carboxylic acid;BBL001494;NSC108689;NSC164660;NSC334360;STK120235;AKOS000120822;AKOS016042464;(+/-)-N-(tert-Butoxycarbonyl)proline;AB01652;AB02540;AB06403;BS-4221;CS-W014893;NSC-108689;NSC-164660;NSC-334360;BP-10507;SMR000069145;SY005295;SY015413;SY020387;N-tert-Butoxycarbonyl-2-carboxypyrrolidine;1, 1-(1,1-dimethylethyl) ester, (S)-;AM20100450;B4285;BB 0241854;FT-0600221;FT-0601708;FT-0601709;EN300-18190;N-t-butoxycarbonylpyrrolidin-2-carboxylic acid;A26492;M03315;1-(t-butoxycarbonyl)pyrrolidine-2-carboxylic acid;A832313;AG-205/15424478;F0918-0581;(RS)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;(2R)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;Chloro(di-2-norbornylphosphino)(2-dimethylaminomethylferrocen-1-yl)palladium(II)

Chemical Property of 1-(Tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Chemical Property:

• Melting Point: 133-135 °C
• Boiling Point: 337.2 °C at 760 mmHg
• PKA: 4.01±0.20(Predicted)
• Flash Point: 157.7 °C
• PSA: 66.84000
• Density: 1.201 g/cm³
• LogP: 1.40840
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 215.11575802
• Heavy Atom Count: 15
• Complexity: 269

Purity/Quality:

98% ^*data from raw suppliers

(±)-N-(tert-Butoxycarbonyl)proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C(=O)O
• Uses: (±)-N-(tert-Butoxycarbonyl)proline is a useful reagent for the enantiospecific preparation of functionalized hindered triazolopyridinones.

Technology Process of 1-(Tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

There total 90 articles about 1-(Tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 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: 100.0%

1-(tert-butyl) 2-(2-oxo-2-phenylethyl) (S)-pyrrolidine-1,2-dicarboxylate (110345-80-7) → 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 2h; Irradiation;

DOI:10.1021/acscatal.7b02117

Reference yield: 98.0%

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0)

Guidance literature:

(S)-N-(tert-butoxycarbonyl)proline methyl ester; With sodium hydroxide; In methanol; water; for 5h; Reflux;

With hydrogenchloride; In water; pH=3;

DOI:10.1016/j.tet.2010.03.002

Reference yield: 97.0%

C24H27NO5 → 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; Irradiation;

DOI:10.1021/acscatal.7b02117

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

L-proline

carbon dioxide

tert-butyl pyrrolidine-1-carboxylate

Downstream raw materials:

Z-Arg(NO₂)-Pro-Lys(Z)-Pro-OBzl

(S)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-isobutyl ester

N-(tert-butyloxycarbonyl)-prolyl-proline benzyl ester

Boc-L-Pro-Gca-pNA

Refernces

• 1、 Li, Chonglong,Wang, Jihai,Ding, Huiyun. "Recyclable Helical Poly(phenyl isocyanide)-Supported l-Proline Catalyst for Direct Asymmetric Aldol Reaction in Brine". . p. 1180 - 1190. Retrieved 2020/09/07.
• 2、 Du, Yihao,Erdem, Safiye S.,Sari, Ozlem,Whiting, Andrew. "A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State". . . Retrieved 2021/11/17.