Home Cart Sign in  
Chemical Structure| 245660-15-5 Chemical Structure| 245660-15-5
Chemical Structure| 245660-15-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4-((tert-Butyldimethylsilyl)oxy)butan-1-amine is a linker.

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of 4-((tert-Butyldimethylsilyl)oxy)butan-1-amine

CAS No. :245660-15-5
Formula : C10H25NOSi
M.W : 203.40
SMILES Code : NCCCCO[Si](C)(C(C)(C)C)C
MDL No. :MFCD18206129
InChI Key :DVHRNKRBIRBDTE-UHFFFAOYSA-N
Pubchem ID :10750686

Safety of 4-((tert-Butyldimethylsilyl)oxy)butan-1-amine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H227
Precautionary Statements:P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235

Application In Synthesis of 4-((tert-Butyldimethylsilyl)oxy)butan-1-amine

* 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 [ 245660-15-5 ]

[ 245660-15-5 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 24424-99-5 ]
  • [ 245660-15-5 ]
  • [ 176686-14-9 ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine; In dichloromethane; at 0 - 20℃; for 1h; To a solution of <strong>[245660-15-5](4-[tert-butyl(dimethyl)silyl]oxy}butyl)amine</strong> (42 g, 0.20 mol) in dichloromethane (400 ml) and triethylamine (58 ml, 0.413 mol) was added BOC-anhydride (54.12 g, 0.248 mol) at 0 C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ice-cold water. The organic layer was washed with water and brine. The organic layer was then dried over anh. sodium sulfate and concentrated. The residue was purified by silica gel chromatography using (EtOAc/pet ether) to give (60 g, 95%) of the sub-title compound as a colorless oil.
92% In dichloromethane; at 0 - 20℃; for 16h; General procedure: A reaction vessel containing a stirring bar was charged with the appropriate amine dissolved in CH2Cl2 (0.2 M). The solution was cooled to 0 C and di-tert-butyl dicarbonate (1.5 equivalents) was added to the reaction vessel. The reaction was stirred at room temperature for 16 h.
92% In dichloromethane; at 0 - 20℃; for 16h; General procedure: A reaction vessel containing a stirring bar was charged with the appropriate amine dissolved in CH2Cl2 (0.2 M). The solution was cooled to 0 C and di-tert-butyl dicarbonate (1.5 equivalents) was added to the reaction vessel. The reaction was stirred at room temperature for 16 h.
  • 2
  • [ 13325-10-5 ]
  • [ 18162-48-6 ]
  • [ 245660-15-5 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine; for 12h;Inert atmosphere; Preparation of this compound was according to the procedure reported by Krivickas S. J. et al. TBDMSCl (8.2 g, 54 mmol, 1.2 eq) was added to a mixture of 4-aminobutanol (4 g, 45 mmol) and pyridine (8 mL). Stirring was allowed for 12 h. TLC (MeOH/CHCl3 = 5/5) indicated the consumption of 4-aminobutanol (Rf = 0.13) and formation of product 4 (Rf = 0.40). The mixture was then concentrated under reduced pressure at 40 oC to provide a residue, which was dissolved by CH2Cl2 (50 mL). After extraction with satd. NaHCO3 (aq), the organic layer was dried over Na2SO4 and filtered through celite pad to provide the filtrate, which was concentrated under reduced pressure. The residue obtained was purified by flash chromatography using silica gel (50 g) with eluents of Et3N/MeOH/CHCl3=2/10/90 to provide colorless oil 4 in quantitative yield (8.8 g). Spectroscopic data is available in the literature. Anal. C10H25NOSi, MW: 203.4, ESI+ Q-TOF MS, M = 203.2 (m/z), [M+H]+ = 204.2; 1H-NMR (500 MHz, CD3OD): d 0.06 (s, 6H, HTBDMS), 0.90 (s, 9H, HTBDMS), 1.55-1.59 (m, 4H), 2.74 (dd, 2H), 3.66 (dd, 2H).
100% With pyridine; In dichloromethane; for 12h; 2. 4-(tert-butyldimethylsilanyloxy)butan-1-amine (compound of formula 7) Preparation of this compound was according to the procedure reported by Krivickas S. J. et al. Tert-Butyldimethylsiyl Chloride (TBDMSCl) (8.2 g, 54 mmol, 1.2 eq) was added to a mixture of 4-aminobutanol (4 g, 45 mmol) and pyridine (8 mL). Stirring was allowed for 12 h. TLC (MeOH/CHCl3=5/5) indicated the consumption of 4-aminobutanol (Rf=0.13) and formation of compound of formula 7 (Rf=0.40). The mixture was then concentrated under reduced pressure at 40 C. to provide a residue, which was dissolved by CH2Cl2 (50 mL). After extraction with satd. NaHCO3 (aq), the organic layer was dried over Na2SO4 and filtered through celite pad to provide the filtrate, which was concentrated under reduced pressure. The residue obtained was purified by flash chromatography using silica gel (50 g) with eluents of Et3N/MeOH/CHCl3=2/10/90 to provide a colorless oil compound of formula 7 in quantitative yield (8.8 g). Spectroscopic data is available in the literature. Anal. C10H25NOSi, MW: 203.4, ESI+Q-TOF MS, M=203.2 (m/z), [M+H]+=204.2; 1H-NMR (500 MHz, CD3OD): δ 0.06 (s, 6H, HTBDMS), 0.90 (s, 9H, HTBDMS), 1.55-1.59 (m, 4H), 2.74 (dd, 2H), 3.66 (dd, 2H).
100% With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; To a solution of 4-aminobutan-l-ol (2 g, 22 mmol) in dichloromethane (25 mL) at 0C were added triethyl amine (5.67 g, 56 mmol) followed by TBS chloride (5 g, 33 mmol) and the resulting reaction mixture was stirred at room temperature for 16h. The progress of the reaction was monitored by TLC and indicates the completion of the reaction. The reaction mixture was diluted with dichloromethane and washed with water, saturated sodium chloride solution and dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 4- ((tert-butyldimethylsilyl)oxy)butan-l -amine (4.5 g, 100%). DIMS (ESI): m/z 204.14 (M+l).
100% With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; To a solution of 4-aminobutan-l-ol (2 g, 22 mmol) in dichloromethane (25 mL) at 0C were added triethyl amine (5.67 g, 56 mmol) followed by TBS chloride (5 g, 33 mmol) and the resulting reaction mixture was stirred at room temperature for 16h. The progress of the reaction was monitored by TLC and indicates the completion of the reaction. The reaction mixture was diluted with dichloromethane and washed with water, saturated sodium chloride solution and dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 4- ((tert-butyldimethylsilyl)oxy)butan-l -amine (4.5 g, 100%). DIMS (ESI): m/z 204.14 (M+l).
92% With triethylamine; In dichloromethane; at 0 - 20℃; for 4h; To the solution of 4-aminobutanol (20 g, 0.224 mol) in dichloromethane (200 ml) was added triethylamine at 0 C. tert-butyldimethylchlorosilane (33.8 g, 0.224 mol) was added at the same temperature and stirred at room temperature for 4 h. The reaction mixture was diluted with water. The organic layer was washed with water, brine, dried over anh. sodium sulfate and concentrated. The crude product (42 g, 92%) was used for next step without purification.
88% With 1H-imidazole; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; General procedure: A reaction vessel containing a stirring bar under argon` (balloon) was charged with the appropriate alcohol, imidazole (2.5 equivalents) and was dissolved in anhydrous CH2Cl2 (0.2 M). The suspension was cooled to 0 C and tert-butyldimethylsilyl chloride (1.1 equivalents) was added to the reaction vessel. The reaction was stirred at room temperature for 3 h.
88% With 1H-imidazole; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; General procedure: A reaction vessel containing a stirring bar under argon` (balloon) was charged with the appropriate alcohol, imidazole (2.5 equivalents) and was dissolved in anhydrous CH2Cl2 (0.2 M). The suspension was cooled to 0 C and tert-butyldimethylsilyl chloride (1.1 equivalents) was added to the reaction vessel. The reaction was stirred at room temperature for 3 h.
33% With 1H-imidazole; In dichloromethane; at 20℃; for 1h; Synthesis of O-(tert-butyldimethylsilyl)-4-amino-1-butanol. Synthesisof O-(tert-butyldimethylsilyl)-4-amino-1-butanol was adapted from a previous procedure.2Briefly, 4-amino-1-butanol (1.93 mL, 0.021 mol) and imidazole (2.72 g, 0.040 mol) weredissolved in 20 mL CH2Cl2. Tert-butyldimethylchlorosilane (TBDMS-Cl, 3.17 g, 0.021 mol) wasdissolved in 10 mL CH2Cl2 and slowly added to the ethanolamine/imidazole mixture over 5minutes. The reaction was stirred at RT for 1 hour. Deionized water (20 mL) was added, theorganic layer collected, and the aqueous layer washed twice more with CH2Cl2. The combinedorganic layers were dried over CaCl2 and concentrated in vacuo to yield a pale yellow oil (1.4 g;33% yield). ESI [M+H]+1 expected 204.18 Da, observed 204.13 Da
33% With 1H-imidazole; In dichloromethane; at 20℃; for 1.08333h; Synthesis of O-(tert-butyldimethylsilyl)-4-amino-1-butanol was adapted from a previous procedure. (Corson et al. ACS Med. Chem. Lett. 2016, 7(12).) Briefly, 4-amino-1-butanol (1.93 mL, 0.021 mol) and imidazole (2.72 g, 0.040 mol) were dissolved in 20 mL CH2Cl2. Tert-butyldimethylchlorosilane (TBDMS-Cl, 3.17 g, 0.021 mol) was dissolved in 10 mL CH2Cl2 and slowly added to the ethanolamine/imidazole mixture over 5 minutes. The reaction was stirred at room temperature for 1 hour. Deionized water (20 mL) was added, the organic layer collected, and the aqueous layer washed twice more with CH2Cl2. The combined organic layers were dried over CaCl2) and concentrated in vacuo to yield a pale yellow oil (1.4 g; 33% yield). ESI [M+H]+1 expected 204.18 Daltons (Da), observed 204.13 Da.
1H-imidazole; REFERENCE EXAMPLE 2 4-(tert-Butyldimethylsilyloxy)-1-butylamine In a manner similar to that in Reference Example 1, 4-amino-1-butanol was reacted with tert-butyldimethylsilyl chloride in the presence of imidazole to give 4-(tert-butyldimethylsilyloxy)-1-butylamine. 1H-NMR (CDCl3)δ(ppm): 0.09 (s, 6H), 0.91 (s, 9H), 1.58 (m, 4H), 3.32 (q, J=6.3 Hz, 2H), 3.64 (t, J=5.8 Hz, 1H).
With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 24h; Part A; Triethylamine (17.7 mL, 127 mmol), 4-dimethylaminopyridine (70 mg), and t~ butyldimethylsilyJ chloride (18.3 g, 121 mmol) were added to a 0 0C solution of 4-amino- 1-butanol (10.3 g, 116 mmol) in dichloromethane (100 mL). The mixture was allowed to warm to room temperature and was stirred for 1 day. The mixture was poured onto water (100 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 21.6 g of 4-[tert- butyl(dimethyl)sily]]oxy}butan-]-amine as an oil that contained minor impurities.
With triethylamine; In dichloromethane; at 0 - 22℃; for 18h; To a solution of 4-aminobutanol (2.08 mL, 22.44 mmol, Aldrich) in DCM (20 mL) is added TEA (3.44 mL, 24.68 mmol) at 0C. Tert-butyldimethylchlorosilane (3.72 g, 24.68 mmol, Aldrich) is added at the same temperature and stirred at RT for 18 hours. The reaction mixture is diluted with water. The organic layer is washed with water and brine, dried over Mg504, filtered and concentrated to give crude 38a, which is used as such for the next step.
With 1H-imidazole; In dichloromethane; at 20℃; for 2h; A mixture of 4-hydroxybutylamine (4.0 g, 44.9 mmol), tørt-butyldimethyl-silyl chloride (7.4 g, 49.3 mmol) and imidazole (6.7 g, 98.7 mmol) in dichloromethane (150 mL) was stirred at room temperature for 2 hours. The product mixture was washed successively with aqueous NaHCO3, water, EPO <DP n="67"/>and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. This intermediate silylated aminoalcohol was used without further purification. To a mixture of the amine (1.0 g, 4.9 mmol) and benzyloxyacetaldehyde (0.74 g, 4.9 mmol) in dichloroethane (15 mL) at room temperature, sodium triacetoxyborohydride (1.3 g, 6.3 mmol) was added. The reaction mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and aqueous sodium carbonate. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 2% methanol in dichloromethane. Collection and concentration of appropriate fractions afforded the title silyloxybutyl-amine. lH NMR (400 MHz, CDCI3) δ 7.33 -7.25 (m, 5H), 4.51 (s, 2H), 3.60 (m, 4H), 2.79 (br t, J = 4.9 Hz, 2H)52.60 (br t, 2 H), 1.52 (br signal, 5 H), 0.87 (s, 9H), 0.03 (s, 6H).

  • 3
  • [ 120-57-0 ]
  • [ 245660-15-5 ]
  • [ 220627-76-9 ]
  • 4
  • [ 245660-15-5 ]
  • [ 174759-66-1 ]
  • (2S,3S)-3-{(S)-1-[4-(tert-Butyl-dimethyl-silanyloxy)-butylcarbamoyl]-3-methyl-butylcarbamoyl}-oxirane-2-carboxylic acid ethyl ester [ No CAS ]
  • 5
  • [ 245660-15-5 ]
  • [ 245660-14-4 ]
  • (2S,3S)-3-{(S)-1-[4-(tert-Butyl-dimethyl-silanyloxy)-butylcarbamoyl]-3-phenyl-propylcarbamoyl}-oxirane-2-carboxylic acid ethyl ester [ No CAS ]
  • 6
  • [ 245660-15-5 ]
  • [ 245660-13-3 ]
  • (2S,3S)-3-[(S)-1-[4-(tert-Butyl-dimethyl-silanyloxy)-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-oxirane-2-carboxylic acid ethyl ester [ No CAS ]
  • 7
  • 2-methyl-3-oxobutanoic acid [ No CAS ]
  • [ 245660-15-5 ]
  • [ 289618-83-3 ]
  • 8
  • [ 245660-15-5 ]
  • (2S,3S)-3-[[[(1S)-3-phenyl-1-(carboxyl)propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]
  • (2S,3S)-3-[[[(1S)-3-phenyl-1-[[(4-t-butyldimethylsilanyloxybutyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]
  • 9
  • [ 245660-15-5 ]
  • (2S,3S)-3-[[[(1R)-3-phenyl-1-(carboxyl)propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]
  • (2S,3S)-3-[[[(1R)-3-phenyl-1-[[(4-t-butyldimethylsilanyloxybutyl)amino]carbonyl]propyl]amino]carbonyl]-oxiranecarboxylic acid ethyl ester [ No CAS ]
  • 10
  • [ 874620-16-3 ]
  • [ 245660-15-5 ]
  • [ 874620-17-4 ]
  • 11
  • [ 874620-15-2 ]
  • [ 245660-15-5 ]
  • [ 852289-08-8 ]
  • 12
  • [ 245660-15-5 ]
  • [ 58-85-5 ]
  • [ 957829-90-2 ]
  • 13
  • [ 245660-15-5 ]
  • cis-N-(tert-butyldimethylsilyloxybut-1-yl)-4-carboxy-3,4-dihydro-6,7-dimethoxy-3-(3',4'-methylenedioxyphenyl)-1(2H)isoquinolone [ No CAS ]
  • 14
  • [ 245660-15-5 ]
  • [ 176686-15-0 ]
  • 15
  • [ 60656-87-3 ]
  • [ 245660-15-5 ]
  • [ 915065-44-0 ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In 1,1-dichloroethane; at 20℃; A mixture of 4-hydroxybutylamine (4.0 g, 44.9 mmol), tørt-butyldimethyl-silyl chloride (7.4 g, 49.3 mmol) and imidazole (6.7 g, 98.7 mmol) in dichloromethane (150 mL) was stirred at room temperature for 2 hours. The product mixture was washed successively with aqueous NaHCO3, water, EPO <DP n="67"/>and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. This intermediate silylated aminoalcohol was used without further purification. To a mixture of the amine (1.0 g, 4.9 mmol) and benzyloxyacetaldehyde (0.74 g, 4.9 mmol) in dichloroethane (15 mL) at room temperature, sodium triacetoxyborohydride (1.3 g, 6.3 mmol) was added. The reaction mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and aqueous sodium carbonate. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 2% methanol in dichloromethane. Collection and concentration of appropriate fractions afforded the title silyloxybutyl-amine. lH NMR (400 MHz, CDCI3) δ 7.33 -7.25 (m, 5H), 4.51 (s, 2H), 3.60 (m, 4H), 2.79 (br t, J = 4.9 Hz, 2H)52.60 (br t, 2 H), 1.52 (br signal, 5 H), 0.87 (s, 9H), 0.03 (s, 6H).
  • 16
  • [ 3008-40-0 ]
  • [ 814-68-6 ]
  • [ 245660-15-5 ]
  • [ 1005736-34-4 ]
YieldReaction ConditionsOperation in experiment
56% 1,2-Cyclopentanedione and 4-(t-butyldimethylsiloxy)butylamine were condensed, and the resulting imine was acylated with acryloyl chloride in the presence of N,N-diethylaniline to obtain enamide (Compound 1). A TBS group was removed from Compound 1, alcohol (Compound 2) was mesylated, and the resultant was brominated with lithium bromide to obtain Compound 3.
  • 17
  • [ 108-94-1 ]
  • [ 245660-15-5 ]
  • C16H33NOSi [ No CAS ]
  • 18
  • [ 3008-40-0 ]
  • [ 245660-15-5 ]
  • C15H29NO2Si [ No CAS ]
  • 19
  • [ 43083-12-1 ]
  • [ 5098-14-6 ]
  • [ 245660-15-5 ]
  • [ 1019654-30-8 ]
YieldReaction ConditionsOperation in experiment
Part B; Trimethyl orthobutyrate (7.35 mL, 45.8 mmol) was added to a solution of aminomalonitrile/7-toIuenesuIfonate (11.6 g, 45.8 mmol) and triethylamine (6.4 mL, 46 mmol) in tetrahydrofuran (200) mL at room temperature. The solution was heated at reflux for 35 minutes, then was allowed to cool to room temperature. The solution was cooled to 0 0C and a solution of 4-[/er/-butyl(dimethyl)silyl]oxy}butan-l -amine (9.34 g, 45.9 mmol) and triethylamine (6.4 mL) in tetrahydrofuran (50 mL) was added. The reaction was stirred at room temperature for 18 hours, then was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 mL) and water (50 mL). The organic phase was washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, gradient elution with 2-4% methanol in dichloromethane) to afford 7.32 g of 5-amino-l-(4-{(/ert-butyl(dimethyl)silyl]oxy}butyl)- 2-propyl-lH-imidazole-4-carbonitrile.
  • 20
  • [ 1297604-48-8 ]
  • [ 245660-15-5 ]
  • [ 1297604-41-1 ]
  • 21
  • [ 58-54-8 ]
  • [ 245660-15-5 ]
  • [ 1277190-31-4 ]
YieldReaction ConditionsOperation in experiment
70% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.25h;Inert atmosphere; Ethacrynic acid 1 (1.2 g, 4 mmol) was dried through azeotropical distillation with toluene three times. After mixing with DMF (2 mL), the mixture was transferred to a two-neck round-bottom flask followed by charging with HBTU (1.65 g, 4.4 mmol, 1.1 eq), DIEA (0.76 mL, 4.4 mmol, 1.1 eq) and compound 4 (805 mg, 4 mmol, 1 eq) sequentially. Stirring was allowed for 15 min. TLC (MeOH/CHCl3 = 2/8) indicated the consumption of EA 1 (Rf = 0.13) and formation of the product 5 (Rf = 0.40). The mixture was then concentrated at 40 C under reduced pressure and the residue obtained was purified further by flash chromatography using silica gel (100 g) with eluents of EtOAc/n-hexane 3/7 to provide colorless oil 5 in 70% yield (1.35 g).
70% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.25h; 3. N-[4-(t-butyldimethylsilanyloxy)butyl]ethacrynic amide (compound of formula 6) Ethacrynic acid (EA) (1.2 g, 4 mmol) was dried through azeotropical distillation with toluene three times. After mixing with DMF (2 mL), the mixture was transferred to a two-neck round-bottom flask followed by charging with O-Benzotriazol-1-yl-tetramethyluronium (HBTU) (1.65 g, 4.4 mmol, 1.1 eq), N,N-Diisopropylethylamine (DIEA) (0.76 mL, 4.4 mmol, 1.1 eq) and compound of formula 7 (805 mg, 4 mmol, 1 eq) sequentially. Stirring was allowed for 15 min. TLC (MeOH/CHCl3=2/8) indicated the consumption of EA (Rf=0.13) and formation of the compound of formula 6 (Rf=0.40). The mixture was then concentrated at 40 C. under reduced pressure and the residue obtained was purified further by flash chromatography using silica gel (100 g) with eluents of EtOAc/n-hexane 3/7 to provide a colorless oil compound of formula 6 in 70% yield (1.35 g). Anal. C23H35Cl2NO4Si, MW: 488.5, ESI+Q-TOF MS, M=487.2 (m/z), [M+H]+=488.2, [M+Na]+=510.1, [2M+Na]+=997.4; the isotope clusters agree with the presence of Cl*2. 1H-NMR (500 MHz, C6D6): δ 0.04 (s, 6H, HTBDMS), 0.96 (s, 9H, HTBDMS), 1.02 (dd, J=7.5 Hz, 3H, CH2CH3), 1.36-1.48 (m, 4H, CH2), 2.42 (q, J=7.5 Hz, 2H, CCH2CH3), 3.18 (q, J=6.5 Hz, 2H, (CONH)CH2CH2), 3.45 (t, J=6.0 Hz, 2H, CH2CH2OTBDMS), 3.91 (d, J=5.0 Hz, 2H, O(CH2)CONH), 5.26 (s, 1H, C=CH2), 5.43 (s, 1H, C=CH2), 5.85-5.90 (m, 1H, Harom), 6.36 (bs, 1H, NH), 6.63 (dd, J=8.5, 2.0 Hz, 1H, Harom). 13C-NMR (125 MHz, C6D6): δ -5.24 (CH3, TBDMS), 12.63 (CH2CH3), 18.44 (C, TBDMS), 23.90 (CH2CH3), 26.10 (CH3, TBDMS), 26.60 (CH2), 30.16 (CH2), 38.89 (CH2), 62.70 (CH2), 68.50 (CH2), 111.13 (CH, arom), 122.83 (C, C=CH2), 127.29 (CH, arom), 127.57 (CH2, C=CH2), 131.42 (C, arom), 134.42 (C, arom), 150.64 (C, arom), 154.72 (C, arom), 165.87 (C, C=O), 194.76 (C, C=O).
  • 23
  • [ 1140737-38-7 ]
  • [ 245660-15-5 ]
  • 24
  • [ 107-14-2 ]
  • [ 245660-15-5 ]
  • C12H26N2OSi [ No CAS ]
  • 25
  • [ 245660-15-5 ]
  • [ 1430413-48-1 ]
  • 26
  • [ 245660-15-5 ]
  • [ 1430412-89-7 ]
  • 27
  • 2,2-dibromo-1-[(4-benzyloxy)]phenylethanone [ No CAS ]
  • [ 245660-15-5 ]
  • 2-[4-(benzyloxy)phenyl]-N-(4-[(tert-butyl)(dimethyl)silyl]oxy}butyl)-2-oxoacetamide [ No CAS ]
  • 28
  • [ 245660-15-5 ]
  • [ 50-79-3 ]
  • C17H28ClNO3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(I) oxide; copper; potassium carbonate; In 1,2-dimethoxyethane; at 100℃; for 1.5h; A mixture of 38a (532.4 mg, 2.62 mmol), 2-5-dichlorobenzoic acid (250 mg, 1 .309 mmol, Aldrich), potassium carbonate (180.9 mg, 1.309 mmol), copper powder (8.3 mg, 0.131 mmol) and copper(l) oxide (9.4 mg, 0.065 mmol) in DME (3 mL) is heated to 100C for 1 .5 hours. The mixture is cooled to RT, and water is added. The mixture is neutralized with HCI 1 N until slightly acidic (pH 5-6) and then extracted with EtOAc (3x). The organic layers are combined, washed with water (2x), NH4CI saturated (2x) and brine, dried over MgSO4, filtered and concentrated. The residue is purified by Combif lash (Hex/EtOAc 100:0 to 70:30) to afford 38b.
  • 29
  • [ 245660-15-5 ]
  • C17H29ClN2O2Si [ No CAS ]
  • 30
  • [ 18162-48-6 ]
  • [ 245660-15-5 ]
  • 31
  • [ 87184-99-4 ]
  • [ 245660-15-5 ]
  • 32
  • [ 98602-83-6 ]
  • [ 245660-15-5 ]
  • 33
  • 2-(4-((tert-butyldimethylsilyl)oxy)butyl)-2,3-dihydro-1H-isoindole-1,3-dione [ No CAS ]
  • [ 245660-15-5 ]
YieldReaction ConditionsOperation in experiment
3.99 g With hydrazine hydrate; In dichloromethane; at 0 - 20℃; Hydrazine monohydrate (6.74 mL, 139 mmol) was added to a solution of crude 2-(4-((iert-butyldimethylsilyl)oxy)butyl)-2,3-dihydro-lH-isoindole- 1 ,3-dione (9.27 g, 27.8 mmol) in CH2C12 (140 mL) at 0 C and was stirred overnight, allowing the reaction to come to rt. The white precipitate was filtered and the filter cake was washed with ample CH2C12. The crude solution was concentrated in vacuo to afford (4-aminobutoxy)(tert- butyl)dimethylsilane (3.99 g, 71%) as a light yellow oil and was used without further purification. Rf 0.26 (1 :9, MeOH:CH2Cl2 with 1% NH4OH); NMR (400 MHz, CDC13) δ 0.03 (s, 6H), 0.87 (s, 9H), 1.44-1.55 (m, 4H), 1 .61 (br s, 2H), 2.68 (t, J= 6.8 Hz, 2H), 3.60 (t, .7 = 6.2 Hz); l3C NMR (100 MHz, CDC13) δ -5.1 , 18.5, 26.1 , 30.4, 30.5, 42.3, 63.3.
  • 34
  • [ 245660-15-5 ]
  • tert-butyl N-(4-((tert-butyldimethylsilyl)oxy)butyl)-N-(3-((triphenylmethyl)sulfanyl)propyl)carbamate [ No CAS ]
  • 35
  • [ 189950-31-0 ]
  • [ 245660-15-5 ]
  • 12,12,13,13-tetramethyl-1,1,1-triphenyl-11-oxa-2-thia-6-aza-12-silatetradecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In acetonitrile; at 55℃; for 24h; (((3- bromopropyl)sulfanyl)diphenylmethyl)benzene (800 mg, 2.01 mmol) was added to a solution of (4- aminobutoxy)(/ert-butyl)dimethylsilane (1.02 g, 5.03 mmol) in MeCN (20 mL) and the reaction was heated to 55 C for 24 h. After cooling to rt, the reaction was quenched with sat. NaHC03 and extracted three times with EtOAc. The combined organic phases were washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The crude material was purified by column chromatography (Si02, 0: 1 to 1 :4, MeOH:CH2Cl2 with 1% NOH gradient) to give 12,12,13,13- tetramethyl-l ,l ,l -triphenyl-l l -oxa-2-thia-6-aza-12-silatetradecane (852 mg, 82%) as an orange oil. Rf 0.33 (1 :4, MeOH:CH2Cl2 with 1% NH4OH); NMR (400 MHz, CDCI3) δ 0.04 (s, 6H), 0.88 (s, 9H), 1.51-1.52 (m, 4H), 1.60 (quin, J = 7.4 Hz, 2H), 2.17 (t, J = 7.0 Hz, 2H), 2.57 (t, J = 7.2 Hz, 4H), 3.59 (t, J= 6.0 Hz, 2H), 7.17-7.28 (m, 9H), 7.39-7.41 (m, 6H); ,3C NMR (100 MHz, CDCI3) δ -5.1 18.6, 25.9, 26.2, 28.5, 29.9, 30.7, 48.6, 49.5, 63.2, 66.8, 126.8, 128.1, 129.8, 145.1.
 

Historical Records

Technical Information

Categories