215918-38-0|(2S,4S)-1-tert-Butyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylate| Ambeed

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Quality Control of [ 215918-38-0 ] Purity: 98% SDS Specification

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Product Details of [ 215918-38-0 ]

CAS No. :	215918-38-0
Formula :	C₁₂H₂₁NO₅
M.W :	259.30
SMILES Code :	O=C(N1[C@H](C(OC)=O)C[C@H](OC)C1)OC(C)(C)C
MDL No. :	MFCD16621201
InChI Key :	NZGOSPJWFBSVFT-IUCAKERBSA-N
Pubchem ID :	58984888

Safety of [ 215918-38-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Application In Synthesis of [ 215918-38-0 ]

* 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 [ 215918-38-0 ]

[ 215918-38-0 ] Synthesis Path-Downstream 1~34

1
[ 215918-38-0 ]
[ 83623-93-2 ]

Yield	Reaction Conditions	Operation in experiment
95.8%	With water; sodium hydroxide; In methanol; at 60℃; for 8h;	At room temperature, compound BB-29-2 (5.5 g, 21.3 mmol) was dissolved in a mixed solvent of methanol/H2O (30 mL/30 mL), NaOH (1.7 g, 42.6 mmol) was added. The reaction system was heated to 60 C. and stirred for 8 h. After the reaction was complete as detected by TLC, most solvent was removed under reduced pressure and then the mixture was cooled to 0 C. 2N Hydrochloric acid was dripped to adjust pH to 3-4, the mixture was extracted with ethyl acetate (80 mL×3). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated by a rotary evaporator to remove the solvent thereby delivering the target compound BB-29-3 (yellow oil, 5.0 g, yield 95.8%). The product was directly used for the next step without purification. 1H NMR (CDCl3, 400 MHz): δ 4.42-4.14 (m, 1H), 3.99-3.98 (m, 1H), 3.65-3.53 (m, 2H), 3.33 (s, 3H). 2.31-2.05 (m, 2H), 1.47 (s, 9H).
		(2) Synthesis of (2S,4S)-1-(tert-butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid According to the manner similar to that of Example 6(2), the title compound (310 mg) was obtained as a colorless solid from methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylate (350 mg). This intermediate was used for the next reaction without purification.
		1 M LiOH (15 ml, 15 mmol) was added to a solution of methyl ester BB42-a (1.96 g, 7.57 mmol) in THF (15 ml) and the resulting mixture was stirred for at room temperature 5h. The pH of the reaction mixture was adjusted to 5 by addition of 1 N HCI whereafter the mixture was extracted with EtOAc (4x50 ml), dried (Na2S04), filtered and concentrated under reduced pressure which gave the title compound (1.85 g, 100%) which was used without further purification in the next step. MS (ESI):246[M+H]+.

123 mg

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20℃;

To a solution of Cap W-19 Step A (140 mg, 0.540 mmol) in MeOH (2 mL) and THF (2.0 mL) was added a premade solution of lithium hydroxide monohydrate (45.3 mg, 1.080 mmol) in Water (2.0 mL). The formed cloudy solution was stirred at rt overnight. Removed volatiles in vacuo. The remaining aqueous layer was diluted with water (10 mL), and extraxted with ether (10 mL). The separated aqueous phase was cooled with ice and acidified with 2 M HC1 to pH 2, and saturated with NaCl, extracted with EtOAc(10 mL, X3). The combined organic layers were washed with brine, dried over MgSC^, filtered, evaporated in vacuo to yield Cap W-19 (123 mg) as a colorless oil, which solidified upon standing.XH NMR (500MHz, CD3OD) δ 4.42 - 4.22 (m, 1H), 4.05 - 3.93 (m, 1H), 3.69 - 3.56 (m, 1H), 3.45 (dd, J=l 1.5, 2.5 Hz, 1H), 3.31 - 3.24 (m, 3H), 2.47 - 2.17 (m, 2H), 1.56 - 1.37 (m, 9H).

References: [1]Patent: US2017/253614,2017,A1 .Location in patent: Paragraph 0274; 0276.
[2]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 52.
[3]Patent: EP1333025,2003,A1 .
[4]Patent: WO2013/95275,2013,A1 .Location in patent: Page/Page column 66.
[5]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 607.

2
(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester [ No CAS ]
[ 215918-38-0 ]

Yield	Reaction Conditions	Operation in experiment
		(1) Synthesis of methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylate According to the manner similar to that of Example 6(1), the title compound (360 mg) was obtained as a colorless oily substance from methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate (400 mg). MS(ESI pos.)m/z: 282([M+Na]+).

References: [1]Patent: EP1333025,2003,A1 .

Yield	Reaction Conditions	Operation in experiment
		Example 1 (1-Benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinyl)carboxylic acid methyl ester (1-Benzyloxycarbonyl-(4S)-hydroxy-(2S)-pyrrolidinyl)carboxylic acid (25 g, 94.3 mmol) was dissolved in DMF (70 ml), and sodium hydride (60% in oil) (7.73 g, 193.3 mmol) was added at 0C. After stirred at room temperature for 30 minutes, methyl iodide (12.9 ml, 207. 5 mmol) was added dropwise. After stirred at room temperature for 2 hours, water was added, followed by extraction with ethyl acetate two times. The combined extracts were dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel, and the title compound (18g, 65%) was obtained as a colorless oily substance from a hexane: ethyl acetate (3:1-2:3)-eluted part. 1H-NMR (CDCl3) δ: 2.15-2.39 (2H, m), 3.27-3.28 (3H, m), 3.54-3.79 (5H, m), 3.91-4.01 (1H, m), 4.40-4.55 (1H, m), 5.02-5.25 (2H, m), 7.26-7.39 (5H, m). (1-tert-butoxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinyl)carboxylic acid methyl ester

4
[ 215918-38-0 ]
[ 871978-92-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; methanol;	(1-tert-butoxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinyl)carboxylic acid methyl ester (11.5 g, 44.8 mmol) was dissolved in a mixed solution of THF (200 ml) and methanol (100 ml), a 1N aqueous sodium hydroxide solution (90 ml, 90 mmol) was added at room temperature, and the mixture was stirred overnight. THF and methanol were removed under reduced pressure, and this was made weakly acidic with 1N hydrochloric acid, followed by extraction with ethyl acetate two times. The combined extracts were dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane and ethyl acetate to obtain the title compound (9.6 g, 87%) as a colorless needle-shaped crystal. 5-[(1-tert-butoxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinyl)carbonylamino]levulinic acid methyl ester

References: [1]Patent: EP1757602,2007,A1 .
[2]Patent: WO2005/121135,2005,A1 .

5
[ 24424-99-5 ]
[ 75176-19-1 ]
[ 215918-38-0 ]

References: [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 51-52.

6
(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester [ No CAS ]
[ 74-88-4 ]
[ 215918-38-0 ]

Yield	Reaction Conditions	Operation in experiment
87.6%		NaH (587 mg, 24.4 mmol) was added at 0 C to a solution of (2S,4S)-1-tert-butyl 2-methyl 4- hydroxypyrrolidine-1 ,2-dicarboxylate (2 g, 8.15 mmol) in dry DMF (10 ml), and the resulting mixture was stirred under N2 on an ice-water bath for 30 min. Methyl iodide was added and the resulting reaction mixture was stirred at room temperature for 4h, then poured into an ice-water mixture and extracted with EtOAc (4x50 ml). The organic layer was dried, filtered and concentrated and the afforded crude product was purified by column chromatography (p.ether:EtOAc 10:1) which gave the title compound (1.96 g, 87.6%). MS (ESI): 260 [M+H]+.
65.2%		NaH (1.96 g, 48.9 mmol) was suspended in THF (60 mL), cooled to 0 C., compound BB-29-1 (8.0 g, 32.6 mmol) was dripped under nitrogen gas atmosphere. After dripping, the mixture was stirred for 2 h at 0 C. MeI (8.0 g, 48.9 mmol) was added at 0 C., the mixture was stirred at this temperature for further 2.5 h. After the reaction was complete as detected by TLC, the reaction was quenched with H2O (10 mL) and extracted with ethyl acetate (80 mL×3). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to remove the solvent. The residue was subject to silica gel column chromatography (PE/EtOAc=9:1→1:1) to deliver the target compound BB-29-2 (colorless oil, 5.5 g, yield 65.2%). 1H NMR (CDCl3, 400 MHz): δ 4.33-4.25 (m, 1H), 3.93-3.89 (m, 1H), 3.70 (s, 3H), 3.59-3.47 (m, 2H), 3.44 (s, 3H), 2.03-1.98 (m, 2H), 1.43 (s, 9H).
47%	With sodium hydride; In tetrahydrofuran; at 20 - 30℃; for 2h;	A solution of 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate (5 g, 20.39 mmol, 1.00 equiv), sodium hydride (1.63 g, 40.75 mmol, 2.00 equiv), iodomethane (5.7 g, 40.16 mmol, 2.00 equiv) in THF (50 mL) was stirred for 12 h at room temperature. The reaction was quenched by the addition of 50 mL ammonium chloride saturated aqueous solution. The resulting solution was extracted with 3*70 mL of EtOAc and the organic layers combined and concentrated under vacuum. Then the residue was applied onto a silica gel column eluting with EtOAc/petroleum ether (3/7) to afford 2.48 mg (47%) of the title compound as a yellow oil. LCMS (ESI, m/z): 246.13[M+H]

	With silver(l) oxide; In acetonitrile; at 85℃; for 9h;	(1) (2S,4S)-Methyl N-Boc-4-methoxypyrrolidine-2-carboxylate, INT 31 To a solution of (2S,4S)-methyl N-Boc-4-hydroxypyrrolidine-2-carboxylate (3.00 g, 12.23 mmol) in acetonitrile (60 mL) was added silver oxide (2.83 g, 12.23 mmol) followed by iodomethane (15.0 mL, 240.95 mmol). The reaction mixture was stirred at 85 C. for 4 hr. More iodomethane (5.0 mL, 80.32 mmol) was added and the mixture was stirred at 85 C. for an additional 5 hr. The mixture was filtered over a pad of Celite. The filtrated was diluted with diethyl ether and washed with saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was back-extracted with diethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford crude INT 31 as a pale yellow oil. MS (ESI): [M+H]+ 260.3. 1H NMR (DMSO-d6): δ (ppm) rotamers 4.30-4.23 (m, 1H), 3.95-3.91 (m, 1H), 3.64 and 3.61 (s, total 3H), 3.55-3.50 (m, 1H), 3.27-3.21 (m, 1H), 3.17 and 3.16 (s, total 3H), 2.42-2.28 (m, 1H), 2.06-1.97 (m, 1H), 1.41 and 1.34 (s, total 9H).
	With silver(l) oxide; In acetonitrile; at 85℃; for 9h;	(1) (2S,4S)-methyl N-Boc-4-methoxypyrrolidine-2-carboxylate, INT 31 To a solution of (2S,4S)-methyl A/-Boc-4-hydroxypyrrolidine-2-carboxylate (3.00 g, 12.23 mmol) in acetonitrile (60 mL) was added silver oxide (2.83 g, 12.23 mmol) followed by iodomethane (15.0 mL, 240.95 mmol). The reaction mixture was stirred at 85 C for 4 hr. More iodomethane (5.0 mL, 80.32 mmol) was added and the mixture was stirred at 85 C for an additional 5 hr. The mixture was filtered over a pad of Celite. The filtrated was diluted with diethyl ether and washed with saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was back-extracted with diethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford crude INT 31 as a pale yellow oil.MS (ESI): [M+H]+260.3.1H NMR (DMSO-d6): δ (ppm) rotamers 4.30-4.23 (m, 1 H), 3.95- 3.91 (m, 1 H), 3.64 and 3.61 (s, total 3H), 3.55-3.50 (m, 1 H), 3.27-3.21 (m, 1 H), 3.17 and 3.16 (s, total 3H), 2.42-2.28 (m, 1 H), 2.06-1 .97 (m, 1 H), 1 .41 and1 .34 (s, total 9H).
	With silver(l) oxide; In acetonitrile; at 85℃; for 9h;	To a solution of (2S,4S)-methyl N-Boc-4-hydroxypyrrolidine-2-carboxylate (3.00 g, 12.23 mmol) in acetonitrile (60 mL) was added silver oxide (2.83 g, 12.23 mmol) followed by iodomethane (15.0 mL, 240.95 mmol). The reaction mixture was stirred at 85 C for 4 hr. More iodomethane (5.0 mL, 80.32mmol) was added and the mixture was stirred at 85 C for an additional 5 hr. The mixture was filtered over a pad of Celite. The filtrated was diluted with diethyl ether and washed with saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was back-extracted with diethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford crude INT 31 as a pale yellow oil.MS (ESI): [M+H] 260.3. ‘H NMR (DMSO-d6): (ppm) rotamers 4.30-4.23 (m, 1H), 3.95-3.91 (m,1H), 3.64 and 3.61 (s, total 3H), 3.55-3.50 (m, 1H), 3.27-3.21 (m, 1H), 3.17 and 3.16 (s, total 3H), 2.42-2.28 (m, 1H), 2.06-1.97 (m, 1H), 1.41 andl.34 (s, total 9H).

References: [1]Patent: WO2013/95275,2013,A1 .Location in patent: Page/Page column 66.
[2]Patent: US2017/253614,2017,A1 .Location in patent: Paragraph 0274; 0275.
[3]Patent: US2019/330194,2019,A1 .Location in patent: Paragraph 1267.
[4]Patent: US2015/152068,2015,A1 .Location in patent: Paragraph 0317; 0318; 0319.
[5]Patent: WO2015/79417,2015,A1 .Location in patent: Page/Page column 66.
[6]Patent: WO2016/164580,2016,A1 .Location in patent: Page/Page column 270.

7
[ 215918-38-0 ]
[ 1445589-60-5 ]

References: [1]Patent: WO2013/95275,2013,A1 .

8
[ 215918-38-0 ]
[ 1445590-24-8 ]

References: [1]Patent: WO2013/95275,2013,A1 .

9
[ 215918-38-0 ]
C₁₉H₂₄BrNO₆ [ No CAS ]

References: [1]Patent: WO2013/95275,2013,A1 .
[2]Patent: US2017/253614,2017,A1 .

10
[ 215918-38-0 ]
[ 1373164-86-3 ]

References: [1]Patent: WO2013/95275,2013,A1 .
[2]Patent: US2017/253614,2017,A1 .

11
[ 215918-38-0 ]
[ 1433946-58-7 ]

References: [1]Patent: WO2013/95275,2013,A1 .

12
[ 215918-38-0 ]
[ 1373165-22-0 ]

References: [1]Patent: WO2013/95275,2013,A1 .
[2]Patent: US2017/253614,2017,A1 .

13
[ 215918-38-0 ]
[ 1433280-27-3 ]

References: [1]Patent: WO2013/95275,2013,A1 .

14
[ 215918-38-0 ]
[ 1445591-86-5 ]

References: [1]Patent: WO2013/95275,2013,A1 .

15
[ 215918-38-0 ]
[ 1445590-73-7 ]

References: [1]Patent: WO2013/95275,2013,A1 .

16
[ 215918-38-0 ]
C₄₂H₅₂N₆O₅ [ No CAS ]

References: [1]Patent: WO2013/95275,2013,A1 .

17
[ 215918-38-0 ]
[ 1445590-85-1 ]

References: [1]Patent: WO2013/95275,2013,A1 .

18
[ 215918-38-0 ]
[ 1445597-10-3 ]

References: [1]Patent: WO2013/95275,2013,A1 .

19
[ 87691-27-8 ]
[ 74-88-4 ]
[ 215918-38-0 ]

Yield	Reaction Conditions	Operation in experiment
550 mg		To an ice cooled mixture of Sodium hydride (228 mg, 5.71 mmol)(prewashed with hexanes) and DMF (10 mL) was added (2S,4S)-l-(tert- butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (600 mg, 2.59 mmol) as a solid in one portion. The formed slurry was stirred at this temperature for 30 min before addition of iodomethane (0.485 mL, 7.78 mmol) dropwise. The final reaction mixture was stirred at rt overweekend. Poured into water (100 mL), extracted with EtOAc (20 mL, X2). The combined organic layer was washed with water and brine, dried over MgS04, filtered, evaporated in vacuo. The residue was purified by FCC (0% to 50% EtOAc-Hexanes) to afford Cap W-19 Step A (550 mg) as a colorless oil. NMR (500MHz, CD3OD) δ 4.38 (td, J=8.6, 3.2 Hz, 1H), 3.99 (dt, J=5.1, 2.4 Hz, 1H), 3.81 - 3.68 (m, 3H), 3.64 - 3.53 (m, 1H), 3.50 - 3.40 (m, 1H), 2.45 - 2.21 (m, 2H), 1.55 - 1.40 (m, 9H)

References: [1]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 607.

20
[ 215918-38-0 ]
[ 215918-39-1 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium borohydride; In tetrahydrofuran; at 0 - 20℃;	(2) (2S,4S)-N-Boc-2-(hydroxymethyl)-4-methoxypyrrolidine, INT 32 To a solution of INT 31 (3.10 g, 11.96 mmol) in THF (120 mL) at 0 C. was added lithium borohydride solution (2 M in THF, 11.96 mL, 23.91 mmol). The reaction mixture was stirred at RT overnight. The mixture was cooled to 0 C. and poured onto ice water. The mixture was stirred for 15 min at RT, then extracted with diethyl ether. The aqueous layer was back-extracted with diethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford crude INT 32 as a colorless oil. MS (ESI): [M+H]+ 232.3. 1H NMR (DMSO-d6): δ (ppm) 4.64 (t, 1H), 3.87 (s, 1H), 3.68-3.44 (m, 3H), 3.32-3.26 (m, 1H), 3.21 (s, 3H), 3.18-3.15 (m, 1H), 2.04-1.97 (m, 1H), 1.42-1.34 (m, 1H), 1.40 (s, 9H).
	With lithium borohydride; In tetrahydrofuran; at 20℃;	(2) (2S,4S)-N-Boc-2-(hydroxymethyl)-4-methoxypyrrolidine, INT 32 To a solution of INT 31 (3.10 g, 1 1 .96 mmol) in THF (120 mL) at 0 C was added lithium borohydride solution (2 M in THF, 1 1.96 mL, 23.91 mmol). The reaction mixture was stirred at RT overnight. The mixture was cooled to 0 C and poured onto ice water. The mixture was stirred for 15 min at RT, then extracted with diethyl ether. The aqueous layer was back-extracted with diethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford crude INT 32 as a colorless oil.MS (ESI): [M+H]+232.3.1H NMR (DMSO-d6): δ (ppm) 4.64 (t, 1 H), 3.87 (s, 1 H), 3.68- 3.44 (m, 3H), 3.32-3.26 (m, 1 H), 3.21 (s, 3H), 3.18-3.15 (m, 1 H), 2.04-1 .97 (m, 1 H), 1.42-1 .34 (m, 1 H), 1 .40 (s, 9H).
	With lithium borohydride; In tetrahydrofuran; at 0 - 20℃;	To a solution of INT 31 (3.10 g, 11.96 mmol) in THF (120 mL) at 0 C was added lithium borohydride solution (2 M in THF, 11.96 mL, 23.91 mmol). The reaction mixture was stirred at RT overnight. The mixture was cooled to 0 C and poured onto ice water. The mixture was stirred for 15 mm at RT, thenextracted with diethyl ether. The aqueous layer was back-extracted with diethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated toafford crude INT 32 as a colorless oil.MS (ESI): [M+H] 232.3. ‘H NMR (DMSO-d6): (ppm) 4.64 (t, 1H), 3.87 (s, 1H), 3.68-3.44 (m, 3H),3.32-3.26 (m, 1H), 3.21 (s, 3H), 3.18-3.15 (m, 1H), 2.04-1.97 (m, 1H), 1.42-1.34 (m, 1H), 1.40 (s, 9H).

References: [1]Patent: US2015/152068,2015,A1 .Location in patent: Paragraph 0320; 0321; 0323.
[2]Patent: WO2015/79417,2015,A1 .Location in patent: Page/Page column 66; 67.
[3]Patent: WO2016/164580,2016,A1 .Location in patent: Page/Page column 270; 271.
[4]Patent: WO2005/121135,2005,A1 .

21
[ 121147-94-2 ]
[ 215918-38-0 ]

References: [1]Patent: US2015/152068,2015,A1 .
[2]Patent: WO2015/79417,2015,A1 .

22
[ 74844-91-0 ]
[ 215918-38-0 ]

References: [1]Patent: US2015/152068,2015,A1 .
[2]Patent: WO2015/79417,2015,A1 .

23
[ 215918-38-0 ]
C₁₄H₁₆BrN₃O*(x)ClH [ No CAS ]

References: [1]Patent: US2017/253614,2017,A1 .

24
[ 215918-38-0 ]
3-[3-[1-[2,5-dichloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetyl]-(4S)-methoxy-(2S)-pyrrolidinyl]-5-isoxazol]propionic acid [ No CAS ]