17012-21-4|Methyl 1-benzylpyrrolidine-3-carboxylate| Ambeed

CAS No. :	17012-21-4
Formula :	C₁₃H₁₇NO₂
M.W :	219.28
SMILES Code :	O=C(C1CN(CC2=CC=CC=C2)CC1)OC
MDL No. :	MFCD04038678
InChI Key :	GDWFCUOFVSNTTG-UHFFFAOYSA-N
Pubchem ID :	4610751

Safety of [ 17012-21-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 17012-21-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.46
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	66.23
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.7
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.15
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.86
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.11
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.91

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.32
Solubility	1.06 mg/ml ; 0.00484 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.99
Solubility	2.26 mg/ml ; 0.0103 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.1
Solubility	0.174 mg/ml ; 0.000794 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.4 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.02

Application In Synthesis of [ 17012-21-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 17012-21-4 ]
Downstream synthetic route of [ 17012-21-4 ]

[ 17012-21-4 ] Synthesis Path-Upstream 1~1

1
[ 17012-21-4 ]
[ 188527-21-1 ]

References: [1] Patent: CN104817549, 2017, B, .

[ 17012-21-4 ] Synthesis Path-Downstream 1~54

1
[ 75-21-8 ]
[ 17012-21-4 ]
[ 119102-90-8 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

2
[ 50-00-0 ]
[ 141-32-2 ]
[ 17136-36-6 ]
[ 17012-21-4 ]

References: [1]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 4079 - 4090.

3
[ 17012-21-4 ]
[ 105-36-2 ]
[ 142483-57-6 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2392 - 2406.

4
[ 93102-05-7 ]
[ 292638-85-8 ]
[ 17012-21-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 17h;	A solution of B1_3 (22.06 g,92.7 mmol) and methyl acrylate (C2, 11.54 g, 139.0 mmol) inDCM(100 mL) was cooled to 0 C.Asolutionof trifluoroacetic acid (12.71 g, 111.2 mmol) in DCM (50 mL) was added slowly by drop to the reactionmixture. The solution was warmed to room temperature and stirred for 17 h. NaHCO 3 saturatedsolution (150 mL) was added to the solution and stirred until no gas was produced. The mixture waspartitioned between water and DCM. The organic phase was washed with brine, dried over Na2SO4and concentrated to give the title compound (19.53 g, 96%). 1H-NMR (CDCl3) 7.35-7.23 (m, 5H),3.69 (s, 3H), 3.64 (s, 2H), 3.12-2.99 (m, 1H), 2.98-2.87 (m, 1H), 2.79-2.69 (m, 1H), 2.69-2.57 (m, 1H),2.58±2.48 (m, 1H), 2.17±2.04 (m, 2H). MS (ESI, pos, ion): 219.9 [M+ H]+.
96.8%	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃;	A solution of 3 (23.5g, 98.98mmol) and methyl acrylate (12.8g, 148.48mmol) in DCM (100 mL) was treated with TFA (13.5 g, 118.78 mmol) in DCM (50 mL) at 0C. The mixture was stirred at 0C for 0.5h, overnight at room temperature. The saturated aqueous NaHCO3 solution was added in the mixture, and it was stirred for 2h. The organic phase was washed with brine, dried with anhydrous Na2SO4, and concentrated in vacuo to give the compound 4 (21.01g, 96.8%).
1420 g	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃;Large scale;	To a 250 mL multi-vial was added 1530.0 g (6.5 mol) of benzylmethoxymethyltrimethylsilylmethylamine,31.80 g (3.7 mol)Methyl acrylate and 38 mL of dichloromethane,A solution of 44.0 g (0.4 mol) of trifluoroacetic acid at a mass concentration of 10% was slowly added dropwise at 0 C,After completion of the dropwise addition, the mixture was stirred at room temperature overnight, and the mixture was concentrated under reduced pressure,The residueRespectively, washed with saturated sodium bicarbonate solution and saturated sodium chloride solution,Combined organic phase,The organic phase passes through anhydrous sulfuric acidSodium drying, filtration,The filtrate was concentrated under reduced pressure,To obtain 1420.0 g of crude 1-benzylpyrrolidine-3-carboxylate as a crude product 100%.

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4861 - 4866.
[2]Organic Process Research and Development,2009,vol. 13,p. 292 - 296.
[3]Molecules,2019,vol. 24.
[4]Bioorganic Chemistry,2021,vol. 114.
[5]Synthesis,2006,p. 2646 - 2648.
[6]Synlett,2015,vol. 26,p. 1815 - 1818.
[7]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 2762 - 2766.
[8]Tetrahedron Letters,2011,vol. 52,p. 3266 - 3270.
[9]Patent: CN104817549,2017,B .Location in patent: Paragraph 0036-0038.

5
[ 93102-06-8 ]
[ 292638-85-8 ]
[ 17012-21-4 ]

References: [1]Chemistry Letters,1984,p. 1117 - 1120.

6
[ 17012-21-4 ]
[ 848413-77-4 ]

Yield	Reaction Conditions	Operation in experiment
88.7%		2-Pyrrolidin-3-ylmethyl-1H-pyrrolo[2,3-b]pyridine. (Compound 66); 8.83 g (91 mmol) methoxymethylamine. (HCl salt) was stirred in 200 ml anhydrous benzene (0 C., under N2). 46.2 ml trimethylaluminium/toluene (2.5M) was added and the mixture was stirred for 2.5 hours at 0 C. Compound 62 (6.73 g, 30.7 mmol) dissolved in 100 ml benzene was added and the resulting mixture was stirred for 1 hour at room temperature. To the mixture was added subsequently saturated NaHCO3 (0 C.) and ethyl acetate. The organic layer was washed three times with a 5% NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (MeOH/ethyl acetate (1/9)) to give 1-benzyl-pyrrolidine-3-carboxylic acid methoxy-methyl-amide (compound 63, 6.76 g, 88.7%).1H-NMR (400 MHz, CDCl3): δ 7.38-7.22 (m, 5H), 3.69-3.62 (m, 5H), 3.45-3.35 (m, 1H), 3.19-3.18 (2×s, 3H), 3.06-2.99 (m, 1H), 2.88-2.81 (m, 1H), 2.56-2.41 (m, 2H), 2.14-2.03 (m, 2H).

References: [1]Patent: US2008/9514,2008,A1 .Location in patent: Page/Page column 24.

7
[ 17012-21-4 ]
1-boc-pyrrolidine-3-carboxylic acid [ No CAS ]

References: [1]European Journal of Organic Chemistry,2005,p. 673 - 682.
[2]Organic Letters,2005,vol. 7,p. 3287 - 3289.

8
[ 17012-21-4 ]
3-iodo-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]European Journal of Organic Chemistry,2005,p. 673 - 682.

9
[ 617-52-7 ]
[ 17012-21-4 ]

References: [1]European Journal of Organic Chemistry,2005,p. 673 - 682.
[2]Chemistry - A European Journal,2017,vol. 23,p. 2005 - 2009.

10
[ 100-46-9 ]
polymer-supported formate [ No CAS ]
[ 17012-21-4 ]

References: [1]European Journal of Organic Chemistry,2005,p. 673 - 682.

11
[ 17012-21-4 ]
[ 862885-08-3 ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.

12
[ 17012-21-4 ]
[ 862885-19-6 ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.
[2]Organic Letters,2005,vol. 7,p. 3287 - 3289.

13
[ 17012-21-4 ]
[ 862885-09-4 ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.

14
[ 17012-21-4 ]
N-(2-(trimethylsilyl)ethoxymethyl)-N-(4-methoxyphenyl)-1-{tert-butoxycarbonyl}-pyrrolidine-3-carboxamide [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.

15
[ 17012-21-4 ]
C₂₃H₃₇⁽²⁾HN₂O₅Si [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.

16
[ 17012-21-4 ]
[ 862885-10-7 ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.
[2]Organic Letters,2005,vol. 7,p. 3287 - 3289.

17
[ 17012-21-4 ]
[ 862885-17-4 ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.

18
[ 17012-21-4 ]
[ 146309-33-3 ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.
[2]Organic Letters,2005,vol. 7,p. 3287 - 3289.

19
[ 17012-21-4 ]
[ 136316-07-9 ]

References: [1]Organic Letters,2005,vol. 7,p. 3287 - 3289.
[2]Organic Letters,2005,vol. 7,p. 3287 - 3289.

20
[ 17012-21-4 ]
[ 785815-76-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4861 - 4866.

21
[ 17012-21-4 ]
[ 849812-22-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4861 - 4866.

22
[ 17012-21-4 ]
[hydroxy-(1-tetradecyl-pyrrolidin-3-yl)-methyl]-phosphonic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4861 - 4866.

23
[ 17012-21-4 ]
[ 849812-30-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4861 - 4866.

24
[ 53215-95-5 ]
[ 17012-21-4 ]

References: [1]Chemistry Letters,1984,p. 1117 - 1120.
[2]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 2762 - 2766.
[3]Patent: US2015/45408,2015,A1 .
[4]Patent: CN104817549,2017,B .
[5]Molecules,2019,vol. 24.
[6]Bioorganic Chemistry,2021,vol. 114.

25
[ 17012-21-4 ]
[ 119102-24-8 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.
[2]Tetrahedron Letters,1991,vol. 32,p. 1245 - 1246.

26
[ 17012-21-4 ]
[ 119102-91-9 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.
[2]Tetrahedron Letters,1991,vol. 32,p. 1245 - 1246.

27
[ 17012-21-4 ]
[ 119103-15-0 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

28
[ 17012-21-4 ]
[ 119103-16-1 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

29
[ 17012-21-4 ]
1-Aza-bicyclo[2.2.1]heptane-4-carboxylic acid hydrazide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

30
[ 17012-21-4 ]
C₉H₁₅N₃O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

31
[ 17012-21-4 ]
1-Benzyl-3-(2-bromo-ethyl)-pyrrolidine-3-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

32
[ 17012-21-4 ]
[ 119102-22-6 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

33
[ 17012-21-4 ]
[ 119102-27-1 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

34
[ 17012-21-4 ]
[ 119102-33-9 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2726 - 2735.

35
N-benzyl-N-(trimetylsilyl)-aminoacetonitrile [ No CAS ]
[ 292638-85-8 ]
[ 17012-21-4 ]

References: [1]Patent: EP1221441,2002,A2 .Location in patent: Page 199.

36
[ 17012-21-4 ]
[ 506-68-3 ]
methyl 1-cyano-3-pyrrolidinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 0.5h;Heating / reflux;	[0151] Following general procedure 5, to a cold (0 C.), stirred solution of amide (20) (32.7 g, 1 equiv.) in THF (70 mL) was added, dropwise, a solution of BH3-Me2S in THF (2 M, 140 mL, 2 equiv.). The resultant mixture was then heated to reflux for 2 h. The reaction was cooled to 0 C. and MeOH was added (25 mL). This mixture was stirred under reflux for 3 h and then cooled to rt. The solution was concentrated under reduced pressure and to the resultant residue was added ice (30 g) and 10 N NaOH until the pH of the mixture was adjusted to pH 9. The mixture was then extracted with CH2Cl2 (2×), dried (MgSO4) and concentrated under reduced pressure to afford the desired benzyl amine which was purified by distillation (bp 125-135 C., 1-2 mm Hg) of the benzyl amine. To a solution of the benzyl amine (219 mg, 1 equiv.) in CH2Cl2 (5 mL) was added a solution of BrCN in CH2Cl2 (1 M, 1.5 mL, 1.5 equiv.). The mixture was refluxed for 30 min, cooled to rt and concentrated under reduced pressure. The resultant residue was purified by flash chromatography (gradient elution 20% EtOAc in hexane to 50% EtOAc in hexane) to afford the desired methyl 1-cyano-3-pyrrolidinecarboxylate (21).

References: [1]Patent: US2003/229226,2003,A1 .Location in patent: Page column 14.

37
[ 17012-21-4 ]
pyrrolidine-3-carboxylic acid methyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97.5%	With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In 1,4-dioxane; methanol; at 50℃; for 5h;	A solution of 4a (5g, 22.80mmol) in MeOH (150 mL) and 4M HCl in dioxane (5.7mL, 22.80mmol) were treated with 10% Pd/C (500mg) of hydrogen at 50oC for 5h. The solid was filtered off and the filtrate was concentrated to give the compound 5a (3.68g, 97.5%).
94%	With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In 1,4-dioxane; methanol; at 50℃; for 5h;	A solution of B1_4(19.50 g, 88.99 mmol), HCl dioxane solution (22.3 mL, 88.99 mmol) in methanol (150 mL) was treatedwith 10% Pd/C (1.95 g) and stirred at 50 C under hydrogen atmosphere for 5 h. The solid was filteredo and the filtrate was concentrated to give the title compound (13.85 g, 94%).
	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In methanol; water;	Reference Example 134 To a solution of <strong>[17012-21-4]methyl 1-benzylpyrrolidine-3-carboxylate</strong> in methanol (50 ml) and 1 N hydrochloric acid (16.9 ml) was added palladium carbon (10%, 1.8 g), and the mixture was stirred overnight under a hydrogen atmosphere. The insolubles were removed by filtration, and then the solvent was distilled off under reduced pressure. Toluene was added thereto, and then the solvent was again distilled off under reduced pressure to give methyl pyrrolidine-3-carboxylate hydrochloride (2.71 g) as a yellow oily material. 1H-NMR (300 MHz, DMSO-d6) δ 1.95-2.25 (2H, m), 3.11-3.45 (5H, m), 3.66 (3H, s), 9.23 (2H, br).

References: [1]Bioorganic Chemistry,2021,vol. 114.
[2]Molecules,2019,vol. 24.
[3]Patent: EP1593673,2005,A1 .Location in patent: Page/Page column 93.

38
[ 17012-21-4 ]
[ 109-89-7 ]
[ 17341-93-4 ]
[ 591781-13-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; hydrogenchloride; methanol; dichloromethane; chloroform; acetonitrile;	RF 0.38 (19:1 dichloromethane-methanol) A solution of 1-benzyl-pyrrolidine-3-carboxylic acid methyl ester (109.6 mg, 0.5 mmol) in 2N hydrochloric acid (3 mL) and dioxane (1 mL) was heated to 80-90 C. for 1 h. The solvent was evaporated under vacuum and the residue redissolved in dioxane/methanol/toluene and evaporated under vacuum. The residue was then heated under reflux in chloroform containing an excess of thionyl chloride for 1 h and then the solvent was evaporated under vacuum. The residue was dissolved in anhydrous dichloromethane (5 mL) and diethylamine (300 μL) was added. After 20 minutes the solvent was evaporated and the residue dissolved in dichloromethane, washed with dilute sodium hydroxide, dried over anhydrous sodium sulfate and evaporated under vacuum. This material was dissolved in anhydrous acetonitrile (2 mL) and 2,2,2-trichloroethyl chloroformate (1.1 eq, 76 μL) was added at room temperature. After 1.5 h a further aliquot of the chloroformate (0.52 eq., 36 μL) was added. After 30 minutes thin layer chromatography (5% methanol-dichloromethane) indicated that the reaction was still incomplete so a further aliquot of the chloroformate (0.52 eq., 36 μL) and N,N-diisopropylethylamine (0.2 eq., 20 μL) was added. After 1 h the reaction was diluted with dichloromethane, washed with dilute sodium hydroxide, dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by chromatography on silica gel eluding with 40:1 dichloromethane-methanol to give 3-diethylcarbamoyl-pyrrolidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester (102.2 mg, 60%) MS: 345.2 [M+H]+

References: [1]Patent: US2003/187254,2003,A1 .

39
[ 51535-00-3 ]
borane tetrahydrofuran [ No CAS ]
[ 17012-21-4 ]

Yield	Reaction Conditions	Operation in experiment
3%	With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; dichloromethane;	EXAMPLE 218 1-[1-(Anthracene-9-carbonyl)-piperidin-4-yl]-pyrrolidine-3-carboxylic acid diethylamide To a solution of 1-benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (30 mmol, 7 g) in anhydrous tetrahydrofuran (40 ml) was added borane-tetrahydrofuran solution (1M, 50 mmol, 50 mL) at ambient temperature. When gas evolution had subsided the solution was heated under reflux for 75 min then stirred for 16 hr at ambient temperature. Hydrochloric acid (6M) was added dropwise (ca. 5 mL) and the mixture was stirred at ambient temperature for 1 hr before removing the solvent under vacuum. The residue was dissolved in dichloromethane and the solution was washed with dilute sodium hydroxide solution. The dichloromethane solution was then extracted with dilute hydrochloric acid (3), the extracts combined, made basic by addition of sodium hydroxide and extracted with dichloromethane (3). The combined organic extract was dried over anhydrous sodium sulfate and the solvent was removed under vacuum. The product was purified by chromatography on silica gel eluding with 5% methanol-dichloromethane to give 1-benzyl-pyrrolidine-3-carboxylic acid methyl ester (200 mg, 3%). MS: 220.2 [M+H]+

References: [1]Patent: US2003/187254,2003,A1 .

40
[ 17012-21-4 ]
1-benzyl-pyrrolidine-3-carboxylic acid amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; sodium; formamide; In methanol; chloroform; N,N-dimethyl-formamide; isopropyl alcohol;	Step 1 1-Benzyl-pyrrolidine-3-carboxylic acid amide To a mixture of 4.4 g 1-benzyl-pyrrolidine-3-carboxylic acid methyl ester (M. J. Kornet, P. A. Thio, S. E. Tan, J. Organic Chemistry, 33:3637-3639(1968) and 3 g formamide in 10 mL of anhydrous DMF heated to 100 C., a solution of sodium methoxide, from 0.33 g of sodium dissolved in methanol, was added dropwise over 20 minutes. After stirring for 1 h at 100 C., the mixture was allowed to cool to room temperature and added to 100 mL of isopropanol. The mixture was concentrated to dryness. The residue was triturated with 200 mL of chloroform, filtered and concentrated to dryness under reduced pressure. The resulting oil was fairly homogeneous by TLC (development with 90:10 chloroform saturated with ammonia:methanol): 1H NMR (400 MHz, CDCl3): δ7.1 (5H), 4.3 (br s, 2 H), 3.5 (d, 2H), 3.4 (m, 1H), 2.6 (m, 2H), 2.5 (m, 1H), 2.25 (m, 1H), 1.9 (m, 1H).
	With sodium methylate; sodium; formamide; In methanol; N,N-dimethyl-formamide; isopropyl alcohol;	Step 1 1-Benzyl-pyrrolidine-3-carboxylic acid amide To a mixture of 4.4 g of 1-benzyl-pyrrolidine-3-carboxylic acid methyl ester (M. J. Kornet et al., J. Org. Chem., 33:3637-3639(1968)) and 3 g of formamide in 10 mL of anhydrous DMF heated to 100 C. was added a solution of sodium methoxide, from 0.33 g of sodium dissolved in methanol, dropwise over 20 min. After stirring for 1 h at 100 C., the mixture was allowed to cool to rt and added to 100 mL of isopropanol. The mixture was concentrated to dryness. The resulting residue was triturated with 200 mL of chloroform, filtered and concentrated to dryness under reduced pressure. The resulting oil was fairly homogeneous by TLC (development with 90:10 chloroform saturated with ammonia: methanol): 1H NMR (400 MHz, CDCl3): 7.1 (5H), 4.3 (br s, 2 H), 3.5 (d, 2H), 3.4 (m, 1H), 2.6 (m, 2H), 2.5 (m, 1H), 2.25 (m, 1H), 1.9 (m, 1H).

References: [1]Patent: US2002/165241,2002,A1 .
[2]Patent: US2003/119811,2003,A1 .

41
[ 17012-21-4 ]
[ 5731-17-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium sulfate; In tetrahydrofuran;	A. 1-Benzylpyrrolidine-3-methanol To a mixture of <strong>[17012-21-4]methyl 1-benzylpyrrolidine-3-carboxylate</strong> (11.67 g, 50 mmol) and tetrahydrofuran, at 0 C. was added lithium aluminum hydride (3.795 g, 100 mmol). The reaction was warmed to room temperature and refluxed for 24 hours. After cooling to 0 C., the reaction was quenched with saturated sodium sulfate and warmed to room temperature. Tetrahyrofuran (50 mL) and solid sodium sulfate were added to the mixture. After stirring for 1 hour, the mixture was filtered and the filtrate was concentrated and vacuum dried for 3 days to give the title compound as a colorless oil (8.49 g, 88%). 1H-NMR (300 MHz, DMSO-d6): 7.21-7.31 (m, 5H), 4.50 (t, J=5.3 Hz, 1H), 3.51 (s, 2H), 3.20-3.31 (m, 2H), 2.35-2.50 (m, 4H), 2.10-2.27 (m, 1H), 1.70-1.85 (m, 1H), 1.27-1.43 (m, 1H). IS-MS, m/e: 192.4 (m+1).

References: [1]Patent: US6635657,2003,B1 .

42
palladium on carbon (Pd/c) [ No CAS ]
[ 17012-21-4 ]
[ 98548-90-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium formate; In methanol;	Methyl (+-)-3-pyrrolidinecarboxylate may be prepared in the following manner: 0.704 g of 10% palladium on carbon (Pd/C) and then 11.5 g of ammonium formate are successively added at a temperature in the region of 20 C., under an argon atmosphere, to 5 g (22.8 mmol) of methyl (+-)-1-(phenylmethyl)-3-pyrrolidinecarboxylate in solution in 100 cm3 of methanol. After stirring for 3 hours at the reflux temperature, the reaction mixture is filtered on Celite. The Celite is rinsed with 3 times 20 cm3 of methanol. The filtrate is then concentrated to dryness under reduced pressure (2.7 kPa) to give 2.5 g of methyl (+-)-3-pyrrolidinecarboxylate in the form of a colorless oil. CI m/z 130 (MH+).

References: [1]Patent: US2004/224946,2004,A1 .

43
[ 17012-21-4 ]
[ 50893-53-3 ]
[ 24424-99-5 ]
[ 122684-33-7 ]

Yield	Reaction Conditions	Operation in experiment
		[0165] To a stirred solution of the benzyl amine (32) (10 g, 1 equiv.) in dichloroethane (220 mL) was added, dropwise, 1-chloroethylchloroformate (5.91 mL, 1.2 equiv.). The reaction was stirred at rt for 30 min followed by concentration of the mixture under reduced pressure. The residue was dissolved in MeOH (100 mL), refluxed for 20 min and then concentrated under reduced pressure. The residue was then dissolved in CHCl3 (80 mL) and Et3N (19.1 mL, 3 equiv.) and cooled to 0 C. To this mixture was added Boc2O (9.95 g, 1 equiv.) in CHCl3 (20 mL) and the reaction was stirred at rt for 16 h. This mixture was then concentrated under reduced pressure, dissolved in EtOAc and washed with 10% citric acid, H2O and brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution: 20% EtOAc in hexane to 33% EtOAc in hexane) to afford the Boc-protected amine. To a solution of the Boc-protected amine (2.29 g, 1 equiv.) in MeOH (24 mL) was added 1 N NaOH (12 mL, 1.2 equiv.). The mixture was stirred at rt for 3 days and then concentrated under reduced pressure. The residue was poured into a solution of 1 N HCl (10 mL) and 10% citric acid (20 mL). The mixture was extracted with EtOAc (3×) and the combined organic extracts were washed with H2O and brine, dried (MgSO4) and concentrated under reduced pressure to yield the acid (33).

References: [1]Patent: US2003/229226,2003,A1 .Location in patent: Page 16-17.

44
[ 17012-21-4 ]
[ 5731-18-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5087 - 5090.

45
[ 17012-21-4 ]
[ 1087209-93-5 ]

References: [1]Organic Process Research and Development,2009,vol. 13,p. 292 - 296.

46
[ 17012-21-4 ]
[ 75-16-1 ]
[ 351370-67-7 ]

Yield	Reaction Conditions	Operation in experiment
		STEP 1. 2-(1-BENZYLPYRROLIDIN-3-YL)PROPAN-2-OL To a cooled (0 C.) solution of methyl N-benzyl-3-pyrrolidinecarboxylate (1.013 g, 4.62 mmol, Tyger) in THF (50 mL) was added methylmagnesium bromide (3.0M solution in diethyl ether, 7.5 mL, 22.50 mmol) dropwise. After 30 min the mixture was warmed to rt for 2 h. The reaction was cooled (0 C.) and carefully quenched with saturated NH4Cl (50 mL) and then diluted with water (25 mL). The mixture was extracted with EtOAc (3*50 mL) and the combined organic layers were washed with brine and dried over Na2SO4. Concentration in vacuo gave a light-yellow oil. m/z: 220.0 [M+1].

References: [1]Patent: US2010/160280,2010,A1 .Location in patent: Page/Page column 60.

47
[ 17012-21-4 ]
[ 135380-26-6 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 3266 - 3270.
[2]Synlett,2015,vol. 26,p. 1815 - 1818.
[3]Patent: WO2015/128334,2015,A1 .

48
[ 17012-21-4 ]
[ 1313369-60-6 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 3266 - 3270.

49
[ 17012-21-4 ]
[ 1313369-54-8 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 3266 - 3270.

50
[ 17012-21-4 ]
[ 79-22-1 ]
[ 1313369-59-3 ]

Yield	Reaction Conditions	Operation in experiment
63%		To the solution of LDA (2M in THF, 61 mL, 123 mmol) in dry THF (98 mL) at -70C, a solution of methyl l -Benzyl-pyrrolidine-3-carboxylate (9 g, 41 mmol) in dry THF (65 ml) was added dropwise. The mixture was stirred at -70C for 90 minutes, then at -40C for 2 hours. The mixture was cooled to -70C and methyl chloroformate (9.54 mL, 123 mmol) in THF (65 mL) was added dropwise. The reaction was stirred at -70C for 30 minutes. The mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with saturated NH4C1 solution at 0C. Layers were separated and the aqueous phase was washed with EtOAc. Mixed organic layers were washed with brine, dried (MgSO i) and concentrated. The crude product was purified by column chromatography on silica gel (EtOAc/hexane 4/6) to afford compound (13a) (7.19 g, 26 mmol, 63%). 1H NMR (300 MHz, CD3OD) δ 2.41 (t, J = 6.6 Hz, 2H), 2.66 (t, J = 6.6 Hz, 2H), 3.06 (s, 2H), 3.63 (s, 2H), 3.71 (s, 6H), 7.22-7.32 (m, 5H)

References: [1]Synlett,2015,vol. 26,p. 1815 - 1818.
[2]Tetrahedron Letters,2011,vol. 52,p. 3266 - 3270.
[3]Patent: WO2015/128334,2015,A1 .Location in patent: Page/Page column 35.

51
[ 17012-21-4 ]
(S)-3-(3,4-dichloro-benzoyl)-3-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Patent: WO2013/160273,2013,A1 .
[2]Patent: US2015/45408,2015,A1 .

52
[ 17012-21-4 ]
3-propyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester [ No CAS ]

References: [1]Patent: WO2013/160273,2013,A1 .
[2]Patent: US2015/45408,2015,A1 .

53
[ 17012-21-4 ]
3-propyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester [ No CAS ]

References: [1]Patent: WO2013/160273,2013,A1 .
[2]Patent: US2015/45408,2015,A1 .

54
[ 17012-21-4 ]
(S)-1-tert-butoxycarbonyl-3-propyl-pyrrolidine-3-carboxylate (R)-1-phenyl-ethyl-ammonium [ No CAS ]

References: [1]Patent: WO2013/160273,2013,A1 .
[2]Patent: US2015/45408,2015,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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P378
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CAS No.: 17012-21-4

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