[ CAS No. 117633-03-1 ] {[proInfo.proName]}

Name: 117633-03-1|Bicyclo[1.1.1]pentane-1-carbaldehyde|97%
Brand: Ambeed
SKU: A579246
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Quality Control of [ 117633-03-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 117633-03-1 ]

CAS No. :	117633-03-1	MDL No. :	MFCD24393552
Formula :	C₆H₈O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NDLHUBKHNOZDHT-UHFFFAOYSA-N
M.W :	96.13	Pubchem ID :	13999819
Synonyms :

Safety of [ 117633-03-1 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P240-P241-P242-P243-P261-P264-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501	UN#:	1989
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 117633-03-1 ]

* 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 [ 117633-03-1 ]

[ 117633-03-1 ] Synthesis Path-Downstream 1~28

1
[ 107-31-3 ]
[ 98585-81-0 ]
[ 117633-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium 4,4′-di(tert-butyl)biphenyl 1.) THF, -65 to -55 deg C, 45 min, 2.) -78 deg C; Yield given. Multistep reaction;

Reference： [1]Wiberg, Kenneth B.; Waddell, Sherman T. [Journal of the American Chemical Society, 1990, vol. 112, # 6, p. 2194 - 2216]

Yield	Reaction Conditions	Operation in experiment
	d. Bicyclo<2.1.1>keton, mehrere Stufen;

3
[ 117633-03-1 ]
[ 22287-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;	5 EXAMPLE 5: bicyclo[l . l .1 jpentane- 1-ylmethanol: [0095] Bicyclo[ 1.1.1 jpentane- 1 -carbaldehyde was prepared as described herein in Example 4. Bicyclo[ 1.1 .1 Jpentane- 1 -carbaldehyde was re-dissolved in MeOH (0.3 M) and cooled to 0 °C. NaBH4 (1.2 equiv.) was added in one portion, and the suspension was allowed to warm to RT. The mixture was stirred for 1 h and monitored by H NMR spectroscopy. The mixture was quenched by the addition of H20 and extracted with Et20. The combined organics were dried (Na2S04) and concentrated to afford bicyclo[l . l . l ]peiitan-l-ylmefhanol as an oil. ]H NMR (400 MHz, CDCI3) δ 3.70 (s, 2 H), 2.53 (s, 1 H), 1.74 (s, 6 H).

Reference： [1]Current Patent Assignee: RECURIUM IP HOLDINGS LLC - WO2015/134710, 2015, A1 Location in patent: Paragraph 0095

4
[ 7677-24-9 ]
[ 24424-99-5 ]
[ 117633-03-1 ]
2-(bicyclo[1.1.1]pentan-1-yl)-2-((tert-butoxycarbonyl)amino)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: trimethylsilyl cyanide; 1-bicyclo<1.1.1>pentanecarboxaldehyde With ammonia In tetrahydrofuran; methanol at 0 - 50℃; Stage #2: With hydrogenchloride; water at 100℃; for 4.5h; Stage #3: di-<i>tert</i>-butyl dicarbonate With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃;	6 EXAMPLE 6: 2-(bicyclo[ 1 .1.1 jpentan- 1 -yl)-2-{{tert-butoxyc3rbonyl)amirio)acetic acid: [0096] A crude solution of bicyclo[l . l . l]pentane-l-carbaldehyde (1 equiv.) in THF (0.6 M) at 0 °C was treated with a 7 N solution of ammonia (15 equiv.) in MeOH. The solution was then treated with TMSCN (1 .5 equiv.), and the resulting mixture was stirred at 50 °C until complete. Once complete, the mixture was cooled to RT and concentrated to dryness. The residue was re-dissolved in aqueous 6N HC1 (0.3 M) then heated to 100 °C for 4.5 h. The mixture was cooled to RT and quenched by the addition of solid NaHC03 until basic by pH paper. The solution was further diluted with sat. aq. NaHCO;? and dioxane (2: 1). Boc-anhydride (1.2 equiv.) was added, and the mixture was stirred at RT overnight. The mixture was acidified with IN HC1 and extracted with EtOAc (Ax). The combined organics were dried (Na2S0 ) and concentrated to afford a dark oil, which was further purified by reverse phase chromatography (ISCO C18, H20 w/ 0.1 % formic acid/ACN w/ 0.1% formic acid) to provide 2-(bicyclo[ 1.1.1 Jpentan- l -yl)-2-((tert-butoxycarbonyi)amino)acetic acid as a white powder. The product exists in solution as a 5.5: 1 mixture of rotamers. Major rotamer : I NMR (400 MHz, DMSO-d6) δ 12,44 (s, COG//. 1 H), 6.94 id. J ------ 8.0 Hz, 5 H), 3.90 (d. J (0155) = 8.0 Hz, 1 H), 2.44 (s, 1 H), 1 .77- 1.67 (m, 6 H), 1.38 (s, 9 H); LC/MS (APCI) mlz 142.1 [C j 2H19NO4-C5H9O2+H] +.

Reference： [1]Current Patent Assignee: RECURIUM IP HOLDINGS LLC - WO2015/134710, 2015, A1 Location in patent: Paragraph 0096

5
[ 35634-10-7 ]
[ 117633-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: iron(III)-acetylacetonate; phenylsilane; 2,6-di-tert-butyl-4-methyl-phenol / methanol; diethyl ether / 20 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane / 2 h / -10 °C 2.2: 0.17 h / -10 - 20 °C
	Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; ferric(III)oxalate hexahydrate 2.1: diisobutylaluminium hydride / dichloromethane / 2 h / -10 °C 2.2: 0.17 h / -10 - 20 °C

Reference： [1]Current Patent Assignee: RECURIUM IP HOLDINGS LLC - WO2015/134710, 2015, A1
[2]Current Patent Assignee: RECURIUM IP HOLDINGS LLC - WO2015/134710, 2015, A1

6
bicyclo<1.1.1>pentane-1-carbonitrile [ No CAS ]
[ 117633-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: bicyclo<1.1.1>pentane-1-carbonitrile With diisobutylaluminium hydride In dichloromethane at -10℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; water at -10 - 20℃; for 0.166667h;	4 EXAMPLE 4: hicyclo[l . l . Ijpentane-l-carbaldehyde: [ΘΘ94] A solution of bicyclo[ 1.1 .1 Jpentane- 1-carbonitrile (1.0 equiv.) in DC (0.3 M) was cooled to -10 °C and treated with a 1 .0 M solution of DIBAL-H ( 1.4 equiv.). After 2 h, the solution was quenched at - 10 °C with IN HCl and allowed to stir for 10 mins at RT. A 10% aqueous solution of Rochelle's salt was added, and the mixture was stirred until a clear separation of layers occurred. The mixture was extracted with DCM (4x), and the combined organics were dried (Na2S04) then concentrated to afford bicyclo[ 1.1.1 jpentane- 1 - carbaldehyde. FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDC13) δ 9.48 (s, 1 H), 2.53 (s, 1 H), 2.08 (s, 6 H).

Reference： [1]Current Patent Assignee: RECURIUM IP HOLDINGS LLC - WO2015/134710, 2015, A1 Location in patent: Paragraph 0094

7
[ 75-52-5 ]
[ 117633-03-1 ]
1-(bicyclo[1.1.1]pentan-1-yl)-2-nitroethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.2%	With potassium <i>tert</i>-butylate In tetrahydrofuran; <i>tert</i>-butyl alcohol at 5℃; for 1.5h;	56.C 1-(bicyclo[1.1.1]pentan-1-yl)-2-nitroethanol Core 42B (2.6 g, 27.0 mmol) and nitromethane (2.188 mL, 40.6 mmol) were dissolved in tetrahydrofuran (10 mL) and tert-butanol (3 mL). After cooling to <5° C. in an ice bath, potassium tert-butoxide (5.41 mL, 5.41 mmol) solution was added dropwise. After 1 hour, the ice-bath was removed and the mixture was stirred for 30 minutes. The mixture was poured into 40 mL of water and extracted with 3*30 mL of ether. The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. Purification via flash column chromatography, eluting with 0-60% ethyl acetate/heptanes over 20 minutes on a 40 g silica gel column afforded the desired product 1-(bicyclo[1.1.1]pentan-1-yl)-2-nitroethanol (2.22 g, 14.13 mmol, 52.2% yield). 1H NMR (500 MHz, Chloroform-d) δ ppm 4.49-4.38 (m, 1H), 4.36-4.27 (m, 2H), 2.61 (s, 1H), 2.32-2.29 (m, 1H), 1.85-1.78 (m, 6H); MS (DCI+) m/z 175 (M+NH4+).
52%	With potassium <i>tert</i>-butylate In tetrahydrofuran; <i>tert</i>-butyl alcohol at 0 - 5℃; for 1h; Inert atmosphere;

Reference： [1]Current Patent Assignee: ABBVIE INC; GALAPAGOS - US2018/99931, 2018, A1 Location in patent: Paragraph 2161; 2357
[2]Buchman, Marek; Greszler, Stephen N.; Liu, Bo; Searle, Xenia B.; Voight, Eric A.; Zhao, Gang [Journal of Organic Chemistry, 2020, vol. 85, # 11, p. 7620 - 7632]

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[ 22287-28-1 ]
[ 117633-03-1 ]