Boc-(+/-)-trans-2-aminocyclohexanol
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Boc-(+/-)-trans-2-aminocyclohexanol
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CAS No:
121282-70-0
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Formula:
C11H21NO3
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Chemical Name:
Boc-(+/-)-trans-2-aminocyclohexanol
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Synonyms:
trans-N-Boc-2-aminocyclohexanol;tert-butyl (1R,2R)-2-hydroxycyclohexylcarbamate;1R,2R-Boc-2-aMinocyclohexanol;tert-Butyl (trans-2-hydroxycyclohexyl)carbaMate;tert-butyl (2-hydroxycyclohexyl)carbaMate;Trans-tert-butyl 2-hydroxycyclohexyl)carbaMate;tert-Butyl (trans-2-hydroxycyclohexyl)
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CAS No:
Safety Information
P264, P270, P273, P301+P312, P330, P391, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Boc-(+/-)-trans-2-aminocyclohexanol Use and Manufacturing
The product from Part A (8.0 g, 26.2 mmol) was dissolved in cyclohexene (100 mL) and ethanol (150 mL), and Pd/C (2.0 g) was added. The reaction mixture was refluxed for 6 h and filtered through a pad OF CELITENo.. The filtrate was evaporated to afford (1S, 2S)-2-hydroxy-cyclohexyl-carbamic acid tert- butyl ester (5.7 g, 100percent) as a white solid. MS M/Z 216.2 ([M+H]+).20percent palladium dihydroxide on carbon (30 molpercent ; 10.8 g) was added to a solution of benzyl ether 397b (15.7 g) in 300 mL of methanol. The heterogeneous mixture was subjected to hydrogenation at 40 psi until no more starting material was detected by TLC (ethyl acetate/hexanes; 2: 8). The mixture was filtered thru celite and the filtrate was concentrated under reduced pressure. No further purification was carried out for the product 397c (11.1 g; 99percent).To a mixture of (1S, 6S)-11 (27 mg, 0.13 mmol) and 10percent Pd-C (13 mg) under a hydrogen atmosphere, methanol (1.0 mL) was added. The mixture was stirred under the hydrogen atmosphere at room temperature for 10 h. After this time, the catalyst was filtered through a pad of CeliteTo a stirred suspension of (lS, 2S)-(+)-2-aminocyclohexanol hydrochloride (1.04 g, 6.86 mmol) in DCM (20 mL) was added triethylamine (2.39 mL, 17.1 mmol). A solution of di-tert-butyl dicarbonate (1.80 g, 8.23 mmol) in DCM (15 mL) was added dropwise. The reaction mixture was stirred at ambient temperature for 2 hours. The reaction was diluted with DCM and washed successively with IN HC1, saturated aqueous NaHCC'3 and brine, dried and concentrated. The residue was purified by column chromatography (hexane/EtOAc, 1 : 1) to give tert-butyl (l S, 2S)-2- hydroxycyclohexylcarbamate (1.30 g, 88percent).Step A
Computed Properties
Molecular Weight:215.29
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:215.15214353
Monoisotopic Mass:215.15214353
Topological Polar Surface Area:58.6
Heavy Atom Count:15
Complexity:222
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Business licensedTrader Supplier of pharmaceutical intermediates,excipients,plant extracts,food additives,CDMO,fine cheimcals,Octadecanedioic acid,Eicosanedioic AcidInquiryCAS No.: 121282-70-0Grade: Pharmaceutical GradeContent: 99% -
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Boc-(+/-)-trans-2-aminocyclohexanol
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