130403-91-7|(S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one| Ambeed

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CAS No. :	130403-91-7
Formula :	C₁₀H₂₁NO₂Si
M.W :	215.37
SMILES Code :	O=C1NCC[C@@H]1O[Si](C)(C(C)(C)C)C
MDL No. :	MFCD26394938
InChI Key :	QEJCHYKXNFQQSM-QMMMGPOBSA-N
Pubchem ID :	10584804

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

Yield	Reaction Conditions	Operation in experiment
84.5%	With 1H-imidazole; dmap; In dichloromethane; at 20℃; for 5h;	To a mixture of (S)-3- hydroxypyrrolidin-2-one (1 g, 10.0 mmol) in anhydrous DCM (100 mL) were added in sequence imidazole (1.36 g, 20.0 mmol), DMAP (122 mg, 1.0 mmol), and TBSC1 (1.8 g, 12.0 mmol). The reaction mixture was stirred at r.t. for 5 hr, then quenched with ice -water and extracted with DCM. The combined organic layers were dried over anhydrous Na2SC>4 and concentrated under reduced pressure. The residue was purified by column chromatography to give the desired product (1.8 g, 84.5percent yield). LC-MS: m/z 216 (M+H)+.
76%	With 1H-imidazole; dmap; In dichloromethane; at 20℃; for 16h;	Intermediate G. (S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one [0038] <strong>[34368-52-0](S)-3-hydroxypyrrolidin-2-one</strong> (5 g, 49.5 mmol) in DCM (198 ml) was treated with DMAP (0.199 g, 1.632 mmol), imidazole (6.73 g, 99 mmol), and TBDMS-Cl (8.94 g, 59.3 mmol). The reaction mixture was stirred at rt for 16 h, and then was washed with a satd. NaHCO3 solution. The organic layer was concentrated and the crude reaction product was purified by silica gel chromatography eluting with 50percent ethyl acetate in petroleum ether. The desired product was isolated as a white solid (8.1 g, 76percent). LC/MS (M+H)+=216.2. 1H NMR (400 MHz, chloroform-d) delta 6.40 (br. s., 1H), 4.26 (t, J=7.8 Hz, 1H), 3.42-3.34 (m, 1H), 3.29-3.21 (m, 1H), 2.36 (dtd, J=12.7, 7.3, 3.3 Hz, 1H), 2.07-1.96 (m, 1H), 0.91 (s, 9H), 0.15 (d, J=7.0 Hz, 6H).
76%	With 1H-imidazole; dmap; In dichloromethane; at 20℃; for 16h;	A stirred solution of commercial <strong>[34368-52-0](S)-3-hydroxypyrrolidin-2-one</strong> (5 g, 50 mmol) in DCM (198 ml) was treated with DMAP (0.2 g, 1.63 mmol), imidazole (6.73 g, 99 mmol), and TBDMS-Cl (8.94 g, 59 mmol). The reaction mixture was stirred at rt for 16 h, and then was washed with a satd. NaHCO3 solution. The organic layer was concentrated and the crude reaction product was purified by silica gel chromatography, eluting with 50percent ethyl acetate in petroleum ether. The desired product was isolated as a white solid (8.1 g, 76percent). LC/MS (M+H)+=216.2; 1H NMR (400 MHz, chloroform-d) delta 6.40 (br. s., 1H), 4.26 (t, J=7.8 Hz, 1H), 3.42-3.34 (m, 1H), 3.29-3.21 (m, 1H), 2.36 (dtd, J=12.7, 7.3, 3.3 Hz, 1H), 2.07-1.96 (m, 1H), 0.91 (s, 9H), 0.15 (d, J=7.0 Hz, 6H).

73.6%	With 1H-imidazole; dmap; In dichloromethane; at 18 - 25℃; for 16h;Inert atmosphere;	Intermediate 30: (6 -3-(tert-Butyldimethylsilyloxy)pyrrolidin-2-one TBDMS-C1 (2.236 g, 14.84 mmol) was added to (5)-3-hydroxypyrrolidin-2-one (1.25 g, 12.36 mmol), N,N-dimethylpyridin-4-amine (0.060 g, 0.49 mmol) and imidazole (1.683 g, 24.73 mmol) in DCM (50 mL) under nitrogen. The resulting solution was stirred at RT for 16 hours. The reaction mixture was diluted with water extracted twice with DCM (50 mL). The organic layer was dried over MgSC^, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, eluting with 50percent EtOAc in isohexane. Pure fractions were evaporated to dryness to afford (S)-3-(tert- butyldimethylsilyloxy)pyrrolidin-2-one (1.960 g, 73.6 percent) as a white crystalline solid. 1H NMR (400 MHz, CDC13) -0.02 (3H, d), -0.01 - 0.03 (3H, m), 0.75 (9H, s), 1.81 - 1.92 (1H, m), 2.21 (1H, dtd), 3.09 (1H, dt), 3.22 (1H, dddd), 4.10 (1H, t), 5.78 (1H, s).
	With triethylamine; In methanol; dichloromethane;	A mixture of 14 g of (S)-3-hydroxy-2-pyrrolidinone, 45 g of tert-butyldimethylsilyl chloride, 50 ml of triethylamine and 500 ml of dichloromethane was stirred overnight. The solution was washed four times with water, once with brine, dried and concentrated in vacuo. The residue was dissolved in 500 ml of methanol, refluxed overnight and concentrated in vacuo. The residue was purified by chromatography (silica gel), giving 21.5 g of (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyrrolidinone; [alpha]D260 =-52° (dichloromethane); mp 48°-49° C.

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CAS No.: 130403-91-7

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CAS No.: 130403-91-7

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
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Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P320
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
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