774212-79-2|(1R,3S)-1-(Boc-amino)-3-(Cbz-amino)cyclopentane| Ambeed

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CAS No. :	774212-79-2
Formula :	C₁₈H₂₆N₂O₄
M.W :	334.41
SMILES Code :	O=C(N[C@@H]1C[C@H](NC(OC(C)(C)C)=O)CC1)OCC2=CC=CC=C2
MDL No. :	MFCD28398154

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
91%		A solution of ((lR,3S)-3-benzyloxycarbonylamino-cyclopentyl)-carbamic acid tert-butyl ester (4.11 g, 12.3 mmol) in ethanol (IMS grade, 50 mL) was added to a flask containing palladium hydroxide (20%> wt/C, 801 mg, 1.20 mmol) and ethanol (5 mL, IMS grade), under an atmosphere of nitrogen. The reaction mixture was evacuated and stirred under an atmosphere of hydrogen at room temperature overnight. The mixture was filtered through a pad of Celite and washed through with ethanol (IMS grade). The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (gradient: 0 to 10% [2M NH3 in MeOH] in DCM) to afford 1.85 g (75%) of ((lR,3S)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester as a colourless gum. 1H NMR (400 MHz, CDC13): delta 5.40-5.27 (m, 1 H), 4.08-3.95 (m, 1 H), 2.13- 2.03 (m, 1 H), 2.02-1.90 (m, 1 H), 1.89-1.78 (m, 1 H), 1.74-1.60 (m, 1 H), 1.51-1.38 (m, 1 H), 1.44 (s, 9 H), 1.32-1.22 (m, 1 H).
69%		(LR, 3S)-N-BOC-L-AMINOCCLOPENTANE-3-CARBOXYLIC acid (5. 00 g, 21.8 mmol), diphenylphosphoryl azide (4.69 mL, 21.8 mmol), and triethylamine (3.04 mL, 21.8 mmol) were combined in benzene (30 mL) at romm temperature. The mixture was heated to 80 oC and stirred 1 br. Benz, l alcohol (2.26 mL, 21.8 mmol) was added and the mixture was heated to 110oC for 16 hr. The MIXTURE WAS CONCENTRATED and ETHY) ACETATE WAS added. The organic phase was washed with water, saturated aqueous NAHCCL, and brine, , dried over Na2SO4, filtered, and concentrated. The crude Product was purified by flash chromatography (silica gel, 20% ethyl acetate in hexanes) to (1S,3R)-cis-(3-tert-butoxycarbonylamino-cyclopentyl)-carbamic acid benzyl ester (5.00 g, 69%) as a white solid. ESI-MS m/e 335 M + H+; 1H NMR (400 MHZ, DMSO-D6) # 7.25 (m, 5 HOT, 6. S3 (m, 2 H), 4. 98 (s, 2H), 3. 77 (brs, 1 H), 2.13 (dt, J = 12.8, 7.6 Hz, 1 H), 1. 75 (d, J=7. HZ. H), 1. 43 (M. 2H), 1. 3S (s, 9 H), 1.22 (m, 2 H).
66%	With diphenyl phosphoryl azide; triethylamine; In toluene; at 100℃;Inert atmosphere;	To a solution of (1 S,3R)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (10.0 g, 43.6 mmol), phenylmethanol (9.04 mL), and triethylamine (9 mL) in toluene (100 mL) was added diphenyl phosphorazidate (9.7 mL). The reaction was warmed to 100 C and reacted overnight. Themixture was washed with saturated NaHCO3 and extracted with ethyl acetate. The organic phase was evaporated to dryness and was purified by flash column chromatography to yield the title Compound (9.6 g, 66% yield).

66%	With diphenyl phosphoryl azide; triethylamine; In toluene; at 100℃;	To a solution of (1 S,3R)-3 -(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (10.0 g, 43.6 mmol), phenylmethanol (9.04 mL), and triethylamine (9 mL) in toluene (100 mL) was added diphenyl phosphorazidate (9.7 mL). The reaction was warmed to 100 C and reacted overnight. Themixture was washed with saturated NaHCO3 and extracted with ethyl acetate. The organic phase was evaporated to dryness and was purified by flash column chromatography to yield the title compound (9.6 g, 66% yield).
48.2%		(1 S,3R)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid (1.0 g; 4,36 mmol), diphenylphosphorylazide (DPPA) (1 ,24 g; 4,36) and triethyl- amine (0.6 ml; 4,36 mmol) in 30 ml toluene were stirred at 80 C for 1 h. Benzyl alcohol (BzlOH) (0,45 ml; 4,36 mmol) was added to the mixture, which was stirred at 110 C for 14 h. The mixture was evaporated, the residue was dissolved in 10% aqueous sodium hydrogen carbonate solution (10 ml) and extracted 3x with ethyl acetate (10 ml). The combined organic layer were dried over Na2S04, filtered, evaporated to dryness and the residue was purified by flash chromatography (n-heptane:ethylacetate=80:20) to yield 0,75 g (48,2%) ((1S,3R)-3-tert-butoxycarbonylamino-cyclopentyl)-carbamic acid benzyl ester (A) as beige solid; LC/MS : 235 (M+H-BOC).
		To a solution of methyl czs-3-[(fer^butoxycarbonyl)amino]cyclopentanecarboxylate (70.9 g) in MeOH (300 mL) was added aqueous NaOH (NaOH 12.2 g, H2O 15.0 mL). The mixture was stirred at ambient temperature for 16 h and the mixture was evaporated under reduced pressure. To the residue was added 5% KHSO4 (250 mL). The precipitate was collected by filtration and dried at 800C under reduced pressure to give a white solid (87.7 g). To the suspension of above solid (66.8 g) in toluene (500 mL) were added diphenylphosphoryl azide (84.2 g) in toluene (50.0 mL) and Et3N (35.4 g) in toluene (50.0 mL) and the mixture was stirred at 100 0C for 35 min. To the mixture was added benzyl alcohol (33.1 g). The mixture was stirred at 130 0C for 2 h and evaporated under reduced pressure. To the residue were added EtOAc (800 mL) and H2O (600 mL) and the organic layer was EPO <DP n="104"/>separated. The organic layer was dried over MgSO4, filtered, concentrated under reduced pressure and purified by flush chromatography (silica gel, 13% to 25% EtOAc in hexane) to give the title compound (43.8 g).1HNMR (200 MHz, CDCl3, delta): 1.26-1.71 (m, 12H), 1.81-2.08 (m, 2H), 2.30-2.52 (m, IH), 3.82-4.09 (m, 2H), 4.69-4.88 (m, IH), 5.00-5.20 (m, 3H), 7.26-7.41 (m, 5H); ESI MS m/z 335 (M++l, 20%).
	With diphenyl phosphoryl azide; triethylamine; In toluene; at 100℃; for 24h;	(0353) <strong>[261165-05-3](1S,3R)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid</strong> (1.03 g), diphenylphosphoryl azide (DPPA, 1.00 ml), triethylamine (0.929 ml), and benzyl alcohol (0.931 ml) were combined in toluene (10 ml) and stirred at 100 C. for 24 hours. The solution was cooled and chromatographed on silica gel using 10% ethyl acetate/hexanes to give the pure product.

(1R,3S)-1-(Boc-amino)-3-(Cbz-amino)cyclopentane

CAS No.: 774212-79-2

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