[ CAS No. 6453-07-2 ]

Name: 6453-07-2|Dimethyl 4-oxocyclopentane-1,2-dicarboxylate|97%
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Product Details of [ 6453-07-2 ]

CAS No. :	6453-07-2	MDL No. :	MFCD00154556
Formula :	C₉H₁₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GMKJWKXCHOWVDN-UHFFFAOYSA-N
M.W :	200.19	Pubchem ID :	4083807
Synonyms :

Safety of [ 6453-07-2 ]

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

Application In Synthesis of [ 6453-07-2 ]

* 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 [ 6453-07-2 ]

[ 6453-07-2 ] Synthesis Path-Downstream 1~19

1
[ 186581-53-3 ]
[ 1703-61-3 ]
[ 6453-07-2 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2679 - 2682
[2]Journal of the American Chemical Society,1937,vol. 59,p. 744,751

2
[ 67-56-1 ]
[ 1703-61-3 ]
[ 6453-07-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride In methanol at 66℃; for 2h;	13.1 Step 1) dimethyl 4-oxocyclopentane- 1,2-dicarboxylate To a solution of 4-oxocyclopentane-1,2-dicarboxylic acid (20.00 g, 58.09 mmol) in methanol (150 mL)was added thionyl chloride (25.3 mL, 349 mmol) dropwise at rt. The mixture was stirred at 66 °C for 2 hours. The mixture was cooled to rt and quenched with water (200 mL). The resulting mixture was extracted with EtOAc (300 mL). The organic layer was washed with saturated sodium bicarbonate solution (100 mL) and sodium chloride solution (100 mL) in turn, and dried over anhydrous sodium sulfate, and concentrated in vacuo to get the title compound as a white solid (23.26 g, 100%).
	With hydrogenchloride

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2018/133858, 2018, A1 Location in patent: Paragraph 00229
[2]Auwers [Chemische Berichte, 1893, vol. 26, p. 364][Chemische Berichte, 1894, vol. 27, p. 1115]

3
[ 908094-01-9 ]
[ 1703-61-3 ]
[ 6453-07-2 ]

Reference： [1]Banerjee,D.K.; Ram,K.S. [Indian Journal of Chemistry, 1972, vol. 10, p. 1 - 8]

4
[ 6453-07-2 ]
3,4-Bis(hydroxymethyl)cyclopentanon [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride

Reference： [1]Banerjee,D.K.; Ram,K.S. [Indian Journal of Chemistry, 1972, vol. 10, p. 1 - 8]

5
[ 67-56-1 ]
[ 1703-61-3 ]
[ 6453-07-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sulfuric acid; In toluene; at 30 - 70℃;Large scale;	0.831(13.7 mol) of concentrated sulfuric acid is added to a solution of 4.5 kg (26.1 mol) of compound IV in 20 1 of methanol and 30 1 of toluene slowly to maintain the temperature below 30C. The reaction mixture is then stirred at 70C until complete conversion of the compound JY (Ca 1 - 3 h) before concentration to half of its original volume (24 1 distilled). After cooling to 3 0C, 25 1 of water and 6 1 of MeTHF areadded and the reaction mixture is stirred an hour before phase decantation. The water layer is discarded and the organic one is washed with 10 1 of water, 10 1 of saturated sodium bicarbonate solution and 5 1 of brine then concentrated to a final volume of about 9 1. Assay of the so-obtained solution indicates 4.5 kg of compound was obtained. This solution is used as such in the next reaction. Yield: 86%.

Reference： [1]Patent: WO2016/157058,2016,A1 .Location in patent: Page/Page column 22; 32
[2]Synlett,1997,vol. 1997,p. 193 - 194

6
[ 6453-07-2 ]
trans-(3R,4R)-Bis(methoxycarbonyl)cyclopentanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium borohydrid In methanol	5 Example 5 Example 5 trans-(3R,4R)-Bis(methoxycarbonyl)cyclopentanol (5) Sodium borohydride (1.11 g, 0.029 mol) was added to a stirred solution of (1R,2S)-4-oxo-cyclopentane1,2-dicarboxylic acid dimethyl ester (4.88 g, 0.0244 mol) in methanol (300 mL) at 0 °C. After 1 h, the reaction was quenched with 90 mL brine, concentrated and extracted with ethyl acetate. The organic phases were pooled, dried, filtered and concentrated. The crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1) to give 5 (3.73 g, 76%) as a yellow oil.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; MEDIVIR AB - EP1881001, 2008, A1

7
[ 4534-68-3 ]
[ 6453-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: H₂SO₄ 2: Na 3: aq. H₂SO₄ / Heating

Reference： [1]Banerjee,D.K.; Ram,K.S. [Indian Journal of Chemistry, 1972, vol. 10, p. 1 - 8]

8
[ 1641-42-5 ]
[ 6453-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Na 2: aq. H₂SO₄ / Heating

Reference： [1]Banerjee,D.K.; Ram,K.S. [Indian Journal of Chemistry, 1972, vol. 10, p. 1 - 8]

9
[ 67885-96-5 ]
[ 6453-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. H₂SO₄ / Heating

Reference： [1]Banerjee,D.K.; Ram,K.S. [Indian Journal of Chemistry, 1972, vol. 10, p. 1 - 8]

10
[ 6453-07-2 ]
[ 36237-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LiAlH₄ 2: Py

Reference： [1]Banerjee,D.K.; Ram,K.S. [Indian Journal of Chemistry, 1972, vol. 10, p. 1 - 8]

11
[ 6453-07-2 ]
[ 115694-83-2 ]

Yield	Reaction Conditions	Operation in experiment
60.77%	With methanol; sodium tetrahydroborate at -5℃; for 2h;	13.2 Step 2) dimethyl 4-hydroxycyclopentane-1,2-dicarboxylate To a solution of dimethyl 4-oxocyclopentane-1,2-dicarboxylate (10.00 g, 49.95 mmol) in methanol (50 mL) was added sodium borohydride (2.32 g, 60.1 mmol) at -5 °C. After the addition, the mixture was stirred for 2 hours. The mixture was quenched with saturated ammonium chloride solution (10 mL). And then anhydrous sodium sulfate (10 g) was added, the resulting mixture was stirred for 10 mm. The mixture was filtered by suction filtration. The filter cake was washed with EtOAc (10 mLx2). The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (V/V) = 1/1) to give the title compound as a colorless oil (6.14 g, 60.77%).

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2018/133858, 2018, A1 Location in patent: Paragraph 00230

12
[ 6453-07-2 ]
dimethyl 4-benzyloxycyclopentane-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: methanol; sodium tetrahydroborate / 2 h / -5 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Cooling with ice 2.2: 2 h / 20 °C