251326-99-5|(1R,4S)-Methyl 4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate| Ambeed

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CAS No. :	251326-99-5
Formula :	C₁₂H₁₉NO₄
M.W :	241.28
SMILES Code :	O=C(N[C@@H]1C=C[C@H](C(OC)=O)C1)OC(C)(C)C
MDL No. :	MFCD02259717

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

Yield	Reaction Conditions	Operation in experiment
60%		To a solution of LiHMDSin THF (72.9 mL of a 1 M solution, 72.9 mmol, 2.2 eq) at -78 °C under Ar was added a solution of(1R,4S)-methyl 4-((t-butoxycarbonyl)amino)cyclopent-2-enecarboxylate3 (8.00 g, 33.2 mmol, 1 eq) in THF(40 mL) dropwise over 1 hr. After stirringfor 30 min, a solution of t-butyl(2-iodoethoxy)dimethylsilane(13.29 g, 46.4 mmol, 1.4 eq) in THF (20 mL) was added. The solution was kept at -78 °C for 15 min,then gradually warmed to 0 °C over 2 hrs, and kept at 0 °C for 1 hr. 1 N HCl and water were added, the solutionextracted with DCM, the organics combined, dried over MgSO4, andconcentrated. Purification bychromatography (400 g column) eluting with 5 to 20percent EtOAc/heptane afforded compound4 (7.89 g, 60percent). 1HNMR (CHLOROFORM-d) d: 5.76 - 5.85(m, 2H), 4.90 (d, J = 9.0 Hz, 1H), 4.72 - 4.82 (m, 1H), 3.69 (s, 3H), 3.57 -3.64 (m, 2H), 2.24 (dd, J = 13.9, 8.0 Hz, 1H), 2.14 (dd, J = 14.1, 3.5 Hz, 2H),1.71 - 1.82 (m, 1H), 1.40 - 1.50 (m, 9H), 0.84 - 0.90 (m, 9H), 0.03 (s, 6H). ESI-MS (m/z):Calculated for C20H37NO5Si: 422.2 (M+23); found: 422.2.
		Example 1 ((3aS,5S,6aR)-5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H- cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-l,6-naphthyridin-6(5H)- yl)methanone Step A (l S,4S)-methyl 4-((tert-butoxycarbonyl)amino)-l -(2-((tert- butyldimethylsilyl)oxy)ethyl)cyclopent-2-enecarboxylate To a solution of LiHMDS in THF (72.9 mL of a 1 M solution, 72.9 mmol, 2.2 eq) at -78 °C under Ar was added a solution of (lR,4S)-methyl 4-((t- butoxycarbonyl)amino)cyclopent-2-enecarboxylate (prepared according to the procedure of US 20050101628 Al (see page 31 , column 1 , Procedure B, step B)), 8.00 g, 33.2 mmol, 1 eq) in THF (40 mL) dropwise over 1 hr. After stirring for 30 min, a solution of t- butyl(2-iodoethoxy)dimethylsilane (13.29 g, 46.4 mmol, 1.4 eq) in THF (20 mL) was added. The solution was kept at -78 °C for 15 min, then gradually warmed to 0 °C over 2 hrs, and kept at 0 °C for 1 hr. I HCl and water were added, the solution extracted with DCM, the organics combined, dried over MgS04, and concentrated. Purification by chromatography (400 g column) eluting with 5 to 20percent EtO Ac/heptane afforded the title compound of Step A. 1H NMR (CHLOROFORM-d) delta: 5.76 - 5.85 (m, 2H), 4.90 (d, J = 9.0 Hz, 1H), 4.72 - 4.82 (m, 1H), 3.69 (s, 3H), 3.57 - 3.64 (m, 2H), 2.24 (dd, J = 13.9, 8.0 Hz, lH), 2.14 (dd, J = 14.1 , 3.5 Hz, 2H), 1.71 - 1.82 (m, 1H), 1.40 - 1.50 (m, 9H), 0.84 - 0.90 (m, 9H), 0.03 (s, 6H). ESI-MS (m/z): Calculated for C20H37NO5Si: 422.2 (M+23); found: 422.2.

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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Disposal
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CAS No.: 251326-99-5

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CAS No.: 251326-99-5

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[ 251326-99-5 ] Synthesis Path-Downstream 1~2

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed