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Chemical Structure| 609-36-9 Chemical Structure| 609-36-9
Chemical Structure| 609-36-9

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H-DL-Pro-OH is a sulfur-containing precursor for the synthesis of glutathione (GSH), which is essential for maintaining glutathione homeostasis. It is widely used in peptide synthesis and protein research.

Synonyms: H-DL-Pro-OH

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Product Details of H-DL-Pro-OH

CAS No. :609-36-9
Formula : C5H9NO2
M.W : 115.13
SMILES Code : OC(=O)C1CCCN1
Synonyms :
H-DL-Pro-OH
MDL No. :MFCD00005250

Safety of H-DL-Pro-OH

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

Application In Synthesis of H-DL-Pro-OH

* 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.

  • Downstream synthetic route of [ 609-36-9 ]

[ 609-36-9 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 609-36-9 ]
  • [ 498-63-5 ]
YieldReaction ConditionsOperation in experiment
65% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 70℃;Inert atmosphere; DL-Proline (6.0 g, 52.0 mmol) was added slowly and portion wise to a stirred suspension of LiAIH4 (3.0 g, 78.0 mmol) in THF (80 ml_) at 0 °C under nitrogen atmosphere carefully over a period of 30 minutes. The reaction mixture was warmed to room temperature and then heated to reflux for 3 h. The mixture was quenched with 20percent KOH solution at 0 °C slowly (18 - 20 mL). The mixture was filtered through a Celite? pad and washed ith THF. The filtered precipitate was again refluxed with THF for 30 minutes and filtered. The combined filtrates were concentrated to give K1 as pale yellow liquid which is slowly converts to dark brown liquid (3.2 g, 65percent). Rf: 0.1 (10percent MeOH in DCM & 1 drop AcOH, ninhydrin active).
18% To a solution of DL-proline (10Og, 869 mmol) in MeOH (1500 mL) was slowly added SOCl2 at 0 0C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give the crude material that was dissolved in THF (1700 mL) again. To this mixture was added portionwise LiAlH4 (132 g, 3.47 mol) at 0 0C. The resulting mixture was heated at 60 0C overnight. The excess LiAlH4 was quenched with KOH. The reaction mixture was filtered and the solid was washed with MeOH (1000 mL). The combined organic layers were dried, filtered, and concentrated under reduced pressure to give the crude material that was purified by distillation to afford 15.8 g (18percent) of pyrrolidin-2-ylmethanol.
With borane-THF; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20℃; for 16h; To a solution of DL-proline (10.0 g, 86.9 mmol) in THF (20 mL) were added boron trifluoride etherate complex (12.9 g, 91.2 mmol) and borane-tetrahydrofuran (1.0 mol/L THF solution, 100 mL) at 0°C, and the mixture was stirred at room temperature for 16 hr. After completion of the reaction, the mixture was further heated under reflux for 1 hr and cooled to room temperature. THF-water (1:1, 2.5 mL) and 6N sodium hydroxide were successively added to the reaction solution, and the mixture was heated under reflux for 2 hr. The reaction solution was cooled to room temperature, and concentrated under reduced pressure. The residue was washed with diethyl ether. The remaining residue, di-tert-butyl dicarbonate (19.9 g, 91.2 mmol) and potassium carbonate (36.0 g, 260 mmol) were dissolved in diethyl ether-water (100 mL-150 mL), and the mixture was stirred at room temperature for 16 hr. The diethyl ether layer was separated and washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 95:5 - 60:40 - 50:50) to give the title compound (13.6 g, 76percent) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 4.74 (d like, 1H), 3.96 (br s, 1H), 3.74-3.21 (m, 4H), 2.13-1.67 (m, 4H), 1.49 (s, 9H).
With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 10h; Using DL-proline as a starting material, dissolving in tetrahydrofuran, adding lithium aluminum hydride in portions, and reacting for 10 hours at room temperature.TLC detects the progress of the reaction, quenches the reaction, filters, concentrates, and recrystallizes the product to obtain intermediate 1,

  • 2
  • [ 123-75-1 ]
  • [ 64-18-6 ]
  • [ 59378-87-9 ]
  • [ 56-40-6 ]
  • [ 609-36-9 ]
  • 3
  • [ 123-75-1 ]
  • [ 141-53-7 ]
  • [ 59378-87-9 ]
  • [ 56-40-6 ]
  • [ 609-36-9 ]
  • 5
  • [ 4016-63-1 ]
  • [ 609-36-9 ]
  • 1-[2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-8-yl]-pyrrolidine-2-carboxylic acid [ No CAS ]
  • 6
  • [ 50995-48-7 ]
  • [ 609-36-9 ]
  • 7
  • [ 796600-15-2 ]
  • [ 609-36-9 ]
  • 1-(3-chloro-4-cyano-2-methylphenyl)proline [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Heat a slurry of <strong>[796600-15-2]2-chloro-4-fluoro-3-methyl-benzonitrile</strong> (0.4 g, 2.36 mmol) and L-proline (2.11 g, 18.8 mmol) in N-methylmorpholine (1.6 mL) at 200 0C in a microwave for 30 min. Partition the reaction between 2N aqueous hydrochloric acid and ethyl acetate. Separate and extract the organic portion with 2N aqueous sodium hydroxide. Acidify the aqueous extract to pH 1 by adding concentrated EPO <DP n="71"/>hydrochloric acid and back extract into ethyl acetate. Extract the combined organic portions with brine, dry over magnesium sulphate, filter, and concentrate under reduced pressure to give the title compound. (0.395 g, 63%) mass spectrum (m/e): 263(M-I); 1H NMR (300 MHz, CDCl3): delta 8.66(bs,lH0, 7.31(d, IH), 6.75(d, IH), 4.38(t,lH), 3.67(m, IH), 3.10(m,lH), 2.43(m,lH), 2.29(s,3H), 2.20-1.90(m.3H).
  • 8
  • [ 41042-12-0 ]
  • [ 536-74-3 ]
  • [ 609-36-9 ]
  • 3-(2-(phenylethynyl)pyrrolidin-1-yl)-1-propylindolin-2-one [ No CAS ]
  • 9
  • [ 3381-87-1 ]
  • [ 609-36-9 ]
  • [ 1609033-30-8 ]
YieldReaction ConditionsOperation in experiment
89% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate; In toluene; at 110℃; for 96h;Inert atmosphere; General procedure: To a solution of [Cp*IrCl2]2 (0.0025 mmol), amino acid 2(0.65 mmol), and NaHCO3 (0.05 mmol) in toluene (3 mL) under an atmosphere of argon was added alcohol 1 (0.5mmol). The resulting mixture was stirred at 110 C for a certain period of time. The reaction mixture was cooled tor.t., and H2O (5 mL) was then added. The resulting solution was extracted with EtOAc. Purification on silicon gel afforded the desired products 3.
  • 10
  • [ 6374-91-0 ]
  • (E)-3,3,3-trifluoro-1-nitroprop-1-ene [ No CAS ]
  • [ 609-36-9 ]
  • (1'S*,2'R*,3R*,7a'S*)-5,7-dibromo-2'-nitro-1'-(trifluoromethyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% In isopropyl alcohol; for 48h;Reflux; General procedure: 4.2. General procedure for the preparation of spiro[indoline-3,20-pyrrolidin]-2-ones 3 and spiro[indoline-3,30-pyrrolizin]-2-ones 4 and 6 A mixture of corresponding isatin 2 (1.0 mmol) and sarcosine(0.13 g, 1.5 mmol) or proline (0.17 g, 1.5 mmol) was stirred in isopropanol (4 mL), and corresponding nitroalkene 1 (1.0 mmol)was added in one portion. The resulting mixture was stirred atreux for 48 h and the reaction progress was monitored by TLC.Upon completion, the mixture was diluted with brine (10 mL),resulting precipitate was ltered off and washed with water andhexane and vacuum dried. In some cases, additional recrystallisa-tion from the mixture hexane/CH2Cl2 (2:1) was necessary.
  • 11
  • [ 6374-91-0 ]
  • [ 29899-87-4 ]
  • [ 609-36-9 ]
  • (1'S*,2'R*,3R*,7a'S*)-5,7-dibromo-2'-nitro-1'-(trichloromethyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In isopropyl alcohol; for 48h;Reflux; General procedure: 4.2. General procedure for the preparation of spiro[indoline-3,20-pyrrolidin]-2-ones 3 and spiro[indoline-3,30-pyrrolizin]-2-ones 4 and 6 A mixture of corresponding isatin 2 (1.0 mmol) and sarcosine(0.13 g, 1.5 mmol) or proline (0.17 g, 1.5 mmol) was stirred in isopropanol (4 mL), and corresponding nitroalkene 1 (1.0 mmol)was added in one portion. The resulting mixture was stirred atreux for 48 h and the reaction progress was monitored by TLC.Upon completion, the mixture was diluted with brine (10 mL),resulting precipitate was ltered off and washed with water andhexane and vacuum dried. In some cases, additional recrystallisa-tion from the mixture hexane/CH2Cl2 (2:1) was necessary.
  • 12
  • [ 6374-91-0 ]
  • [ 1613308-55-6 ]
  • [ 609-36-9 ]
  • (1'S*,2'R*,3R*,7a'S*)-5,7-dibromo-2'-nitro-1'-(tribromomethyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% In isopropyl alcohol; for 48h;Reflux; General procedure: 4.2. General procedure for the preparation of spiro[indoline-3,20-pyrrolidin]-2-ones 3 and spiro[indoline-3,30-pyrrolizin]-2-ones 4 and 6 A mixture of corresponding isatin 2 (1.0 mmol) and sarcosine(0.13 g, 1.5 mmol) or proline (0.17 g, 1.5 mmol) was stirred in isopropanol (4 mL), and corresponding nitroalkene 1 (1.0 mmol)was added in one portion. The resulting mixture was stirred atreux for 48 h and the reaction progress was monitored by TLC.Upon completion, the mixture was diluted with brine (10 mL),resulting precipitate was ltered off and washed with water andhexane and vacuum dried. In some cases, additional recrystallisa-tion from the mixture hexane/CH2Cl2 (2:1) was necessary.
  • 13
  • [ 20026-96-4 ]
  • [ 485-47-2 ]
  • [ 609-36-9 ]
  • ethyl 12-(4-chlorophenyl)-6,11-dioxo-1,2,3,4,6,11-hexahydro-4,11a-ethenopyrido[1,2-b]isoquinoline-13-carboxylate [ No CAS ]
  • 14
  • [ 59-66-5 ]
  • [ 609-36-9 ]
  • C5H9NO2*C4H6N4O3S2 [ No CAS ]
  • 15
  • [ 6374-91-0 ]
  • [ 26089-39-4 ]
  • [ 609-36-9 ]
  • C42H58Br2N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In methanol; water;Reflux; General procedure: A solution of C3-β-cholestrylcarboxylate (4) (1 mmol), proline (11)(1 mmol) and isatin (1a-f)/acenaphthenequinone (7)/ninhydrin (9)(1 mmol) was stirred in aqueous methanol for 1-2 h at reflux temperature.After the completion of reaction as indicated by TLC, methanolwas evaporated under reduced pressure. The crude product waspurified by column chromatography using hexane:EtOAc mixture (2:1)as an eluent.
  • 16
  • [ 609-36-9 ]
  • [ 108-93-0 ]
  • [ 7731-02-4 ]
  • 17
  • [ 132622-69-6 ]
  • [ 609-36-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; A. Proline Analog Un-Fixing Agent Preparation The proline analog un-fixing agent corresponding to compound (12) ((2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid) was purchased from Sigma-Aldrich and used without further purification (Cat. No. 51-35-4; Sigma-Aldrich Corp., St. Louis, Mo., USA). The proline analog un-fixing agent of compound (13) ((2S,4R)-4-aminopyrrolidine-2-carboxylic acid) was prepared from a Boc protected reagent using the following 1-step procedure. To a solid of <strong>[132622-69-6](2S,4R)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid</strong> (150 mg, 0.7 mmol, 1 equiv) (Catalog#: 132622-69-6, Combi-Blocks) was added 4 mL of 4M HCl and stirred at RT. After stirring at RT for 2 h, the reaction mixture was conc. in vacuo to give the title compound in quantitative yield. 1H NMR (80 MHz, CD3OD): δ=2.53-2.13 (m, 2H), 3.12-2.91 (m, 1H), 3.66-3.12 (m, 2H), 4.13-3.67 (m, 1H). The proline analog un-fixing agent corresponding to compound (14) dihydrochloride ((2S,4S)-4-[(pyridin-4-yl)oxy]pyrrolidine-2-carboxylic acid dihydrochloride) was purchased from Enamine and used without further purification (Cat. No. EN300-7353434; Enamine, New Jersey, USA). The proline analog un-fixing agent of compound (15) ((2S,4S)-4-(Pyridin-3-yloxy)pyrrolidine-2-carboxylic acid) was prepared from a Boc-protected reagent using the following 1-step procedure To a solid of (2S,4S)-1-(tert-butoxycarbonyl)-4-(pyridin-3-yloxy)pyrrolidine-2-carboxylic acid (100 mg, 0.3 mmol, 1 equiv) (Catalog#: PH014404, Sigma Aldrich) was added 2 mL of 4M HCl and stirred at RT. After stirring at RT for 2 h, the reaction mixture was conc. in vacuo to give the title compound in quantitative yield. 1H NMR (80 MHz, CD3OD): δ=2.75-2.05 (m, 2H), 3.51 (br-s, 2H), 4.63-4.25 (m, 1H), 5.61-5.13 (m, 1H), 8.67-7.49 (m, 4H).
 

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