[ CAS No. 159634-80-7 ] {[proInfo.proName]}

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Quality Control of [ 159634-80-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 159634-80-7 ]

CAS No. :	159634-80-7	MDL No. :	MFCD11227124
Formula :	C₁₈H₂₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	302.41	Pubchem ID :	-
Synonyms :

Safety of [ 159634-80-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 159634-80-7 ]

* 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 [ 159634-80-7 ]

[ 159634-80-7 ] Synthesis Path-Downstream 1~14

1
[ 906369-83-3 ]
[ 159634-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; mercaptoacetic acid In N,N-dimethyl-formamide

Reference： [1]Liu, Jian; Jian, Tianying; Sebhat, Iyassu; Nargund, Ravi [Tetrahedron Letters, 2006, vol. 47, # 29, p. 5115 - 5117]

2
[ 159634-80-7 ]
C₂₆H₂₆ClN₂O₃Pol [ No CAS ]
C₄₄H₅₁N₄O₅Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium iodide In N,N-dimethyl-formamide	5 The resin from the previous step (0.1 mmol) was added to a scintillation vial along with 214mg (l.Ommol) of proton sponge, 45mg (0.3mmol) of NaI, 77mg (0.5mmol) of tert-butyl 2,3- dihydro-lH,177-spiro[isoqmnoline-4,4'-piperidine]-r-carboxylate, and 2ml of DMF. The resin was washed with each of the following solvents three times each and dried in vacuo: DMF, H2O, MeOH, and DCM.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2007/136605, 2007, A2 Location in patent: Page/Page column 63; 64

3
C₁₉H₂₁N₃O₄S [ No CAS ]
[ 159634-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOH / ethyl acetate 2: HSCH₂COOH; LiOH / dimethylformamide

Reference： [1]Liu, Jian; Jian, Tianying; Sebhat, Iyassu; Nargund, Ravi [Tetrahedron Letters, 2006, vol. 47, # 29, p. 5115 - 5117]

4
[ 906369-80-0 ]
[ 159634-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂SO₄ / acetic acid 2: NaOH / ethyl acetate 3: HSCH₂COOH; LiOH / dimethylformamide

Reference： [1]Liu, Jian; Jian, Tianying; Sebhat, Iyassu; Nargund, Ravi [Tetrahedron Letters, 2006, vol. 47, # 29, p. 5115 - 5117]

5
[ 40481-13-8 ]
[ 159634-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 95 percent / aq. NaOH / tetrahydrofuran 2: BH₃-THF / 40 °C 3: Et₃N / CH₂Cl₂ 4: H₂SO₄ / acetic acid 5: NaOH / ethyl acetate 6: HSCH₂COOH; LiOH / dimethylformamide

Reference： [1]Liu, Jian; Jian, Tianying; Sebhat, Iyassu; Nargund, Ravi [Tetrahedron Letters, 2006, vol. 47, # 29, p. 5115 - 5117]

6
[ 24424-99-5 ]
[ 159634-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOH / ethyl acetate 2: HSCH₂COOH; LiOH / dimethylformamide

Reference： [1]Liu, Jian; Jian, Tianying; Sebhat, Iyassu; Nargund, Ravi [Tetrahedron Letters, 2006, vol. 47, # 29, p. 5115 - 5117]

7
[ 158144-82-2 ]
[ 159634-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Et₃N / CH₂Cl₂ 2: H₂SO₄ / acetic acid 3: NaOH / ethyl acetate 4: HSCH₂COOH; LiOH / dimethylformamide

Reference： [1]Liu, Jian; Jian, Tianying; Sebhat, Iyassu; Nargund, Ravi [Tetrahedron Letters, 2006, vol. 47, # 29, p. 5115 - 5117]

8
[ 158144-79-7 ]
[ 159634-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: BH₃-THF / 40 °C 2: Et₃N / CH₂Cl₂ 3: H₂SO₄ / acetic acid 4: NaOH / ethyl acetate 5: HSCH₂COOH; LiOH / dimethylformamide

Reference： [1]Liu, Jian; Jian, Tianying; Sebhat, Iyassu; Nargund, Ravi [Tetrahedron Letters, 2006, vol. 47, # 29, p. 5115 - 5117]

9
[ 159634-80-7 ]
[ 75-36-5 ]
[ 159634-81-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at 0℃; for 0.25h;	6 EXAMPLE 6; l-(l'-(4-(ethoxyimino)cycIohexyl)-lH-spiro[isoquinoline-4,4'-piperidine]- 2(3H)-yl)ethanone (Compound No. 196); EPO [00218] tert-Butyl 2,3-dihydro-lH-spiro[isoquinoline-4,4'-piperidine]-r-carboxylate 6a (2.128 g, 6.28 mmol) was dissolved in anhydrous dichloromethane (30 mL), cooled in an ice- H2O bath and treated dropwise with a solution of acetyl chloride (518 mg, 6.59 mmol) in anhydrous dichloromethane (5 mL). The reaction was then treated dropwise with a solution of triethylamine (1.335 g, 13.2 mmol) in anhydrous dichloromethane (5 mL). The reaction was stirred in the ice-H2O bath for 15 minutes, then diluted with dichloromethane (100 mL), washed with H2O, saturated NaHCO3 (3x), saturated brine, dried (Na2SO^ and filtered. The filtrate was concentrated under reduced pressure to afford crude tert-buty 2-acetyl-2,3- dihydro-l H-spiro[isoquinoline-4,4'-piperidine]-r-carboxylate 6b as a colorless oil (2.732 g, quantitative yield).

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - WO2006/58303, 2006, A2 Location in patent: Page/Page column 78-79

10
1,3-dihydro-1,3-dihydroxyspiro[4H-2-benzofuran-4,4'-piperidine]-1'-carboxylic acid, 1,1-dimethylethyl ester [ No CAS ]
[ 159634-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride In methanol	15.B Step B Step B 1,2,3,4-tetrahydrospiro[isoquinolin-4,4'-piperidine]-1'-carboxylic acid, 1,1-dimethylethyl ester The intermediate of Step A (100 mg) was stirred in methanol (2 mL) saturated with ammonia for one day, and evaporated to remove ammonia. The residue was redissolved in methanol (3 mL) and sodium cyanoborohydride (50 mg, excess) was added. The mixture was stirred overnight. Evaporation and purification gave the amine. 1 H NMR (400 MHz, CD3 OD): δ7.35-6.96 (m, 4 H), 4.00 (s, 2 H), 3.14

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5536716, 1996, A

11
[ 159634-80-7 ]
[ 124-63-0 ]
1'-(tert-butoxycarbonyl)-(2-methylsulfonyl)-2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane for 1h;	118 EXAMPLE 118 1-{ [2-(methylsulfonyl)-2,3-dihydro-lH, 1 'H-spiro[isoquinoline-454'-ρiρeridin]~ I1- yl]methyl}-4-oxo-4i:/-quinolizine-3-carboxylic acid To a solution of tert-bntyl 2,3-dihdyro-lH,rH-spro[isoqumoline-4,41- piρeridine]-l'-carboxylate (0.200 g, 0.661 mmol) in 3 mL of dichloromethane was added lriethylamine (0.13 mL, 1.3 mmol) and methanesulfonyl chloride (0.077 mL, 0.99 mmol). After 1 hour, the mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to yield tert-butyl 2-(methylsulfonyl)- 2,3-dihdyro-lH,l'H- spiro[isoquinoline-4,4'-piperidine]-l '-carboxylate as a yellow oil.To a solution of the above carboxylate (0.230 g, 0.604 mmol) in 3 mL CH2Cl2 was added 4 N HCl/dioxane (0.50 mL, 2.0 mmol). After 2 hours, the mixture was concentrated in vacuo to yield 2-(methylsulfonyl)-2,3-dihydro-l//- spiro[isoquinoline-4,4'-piperidine] hydrochloride. [RL-NOP-22539The title compound was prepared by the procedure described in Example 1 to give a mass ion (ES+) m/z of 481.9 calculated for M+H+ [C25H27N3O5S : 481.56] : 1H NMR (400 MHz, CD3OD) δ 9.58 (d, J- 7.4 Hz, IH), 8.77 (s, IH), 8.45 (d, 7= 9.4 Hz, IH), 8.24-8.20 (m, IH), 7.75-7.72 (m, IH), 7.37-7.35 (m, IH), 7.28-7.24 (m, 2H), 7.19- 7.17 (m, IH), 4.47 (s, 2H), 3.66 (s, 2H), 3.78-3.56 (m, 2H), 3.48-3.13 (m, 4H), 2.31-2.28 (m, 2H), 2.07-2.03 (m, 2H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/102574, 2009, A1 Location in patent: Page/Page column 44-45

12
[ 159634-80-7 ]
[ 50-00-0 ]
[ 1181965-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid In water; 1,2-dichloro-ethane for 3h;	117 EXAMPLE 117 A mixture of tert-butyl 2,3-dihydro-lH;rH-spiro[isoquinoHne-4,4'- piperidinej-l'-carboxylate (0.200 g, 0.661 mmol), formaldehyde in water (37%) (0.15 mL, 2.00 mmol), glacial acetic acid (0.15 mL, 2.0 mmol) and 3 mL of dichloroethane was stirred vigorously. To the stirring mixture was added sodium triacetoxyborohydride (0.280 g, 1.32 mmol), which was stirred for 3 hours. The mixture was diluted with DCM, washed with saturated aqueous sodium bicarbonate solution, and then brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to yield tert-butyl 2- methyl- 2,3-dihydro- 1 H, 1 η-spiro[isoquinolme-4,4'-piperidine]- 1 '-carboxylate. ORL-NOP-22539To a solution of the above carboxylate (0.200 g, 0.632 mmol) in 3 mL of DCM was added 4 N HCl/dioxane (0.50 mL, 2.0 mmol). After 2 hours, the mixture was concentrated in vacuo to yield 2-methyl-2.3-dihydro-lH-spiro[isoquinoline-4J4'- piperidine] dihydrochloride .The title compound was prepared by the procedure described in Example 1 to give a mass ion (ES+) rα/z of 418.0 calculated for M+H+ [C25H27N3O3: 417.5]: 1H NMR (400 MHz, CD3OD) δ 9.58 (d, J- 7.4 Hz, IH), 8.72 (s, IH), 8.47 (d, J- 8.8 Hz, IH), 8.19 (t, J= 7.5 Hz, IH), 7.75-7.72 (m, IH), 7.48-7.40 (m, 2H), 7.36-7.33 (m, IH), 7.24 (d, J- 7.3 Hz, IH), 4.78 (s, 2H), 4.47 (s, 2H), 3.65-3.62 (m, 2H), 3.48-3.22 (m, 4H), 3.17 (s, 3H), 2.44-2.32 (m, 2H), 2.20-1.95 (ra, 2H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/102574, 2009, A1 Location in patent: Page/Page column 43-44

13
[ 159634-80-7 ]
2-methyl-2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidine] dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; acetic acid / water; 1,2-dichloro-ethane / 3 h 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/102574, 2009, A1

14
[ 159634-80-7 ]
[ 1181965-82-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 2 h

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/102574, 2009, A1

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[ CAS No. 159634-80-7 ] {[proInfo.proName]}

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Product Details of [ 159634-80-7 ]

Safety of [ 159634-80-7 ]

Application In Synthesis of [ 159634-80-7 ]

[ 159634-80-7 ] Synthesis Path-Downstream 1~14

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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