p-Toluenesulfonic acid monohydrate → 1-(3-amino-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol

HRID 1254322Notes

Reaction equation

CC1C=CC(S(O)(=O)=O)=CC=1.O.C(OC([NH:20][CH2:21][CH:22]([N:31]([CH3:41])[C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[O:33])[CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=O)(C)(C)C>C(O)C.CCOCC>[NH2:20][CH2:21][CH:22]([N:31]([CH3:41])[C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:38])([CH3:40])[CH3:39])=[O:33])[CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

Conditions

Temperature: 62.5 °C

Procedure

A solution of p-TsOH.H2O (25 mg) in ethanol (0.5 mL) was added to 1-(3-(t-butoxy-carbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol (50 mg, 0.12 mmol) dissolved in ether (12 mL). The transfer was completed with additional ether (2 mL). The resulting solution was evaporated under reduced pressure at rt to remove Et2O and heated at 60-65° C. for 20 min under reduced pressure to remove ethanol. The residue was dissolved in MeOH and aqueous K2CO3 was added. The mixture was evaporated and extracted with EtOAc (3×). The combined organic phases were dried over Na2SO4, filtered and evaporated to give 1-(3-amino-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propyl)cyclohexanol (43 mg, 89%). MS m/z 453 (M+Na+).

Workup

customThe resulting solution was evaporated under reduced pressure at rt
customto remove Et2O
customto remove ethanol
dissolutionThe residue was dissolved in MeOH
additionaqueous K2CO3 was added
customThe mixture was evaporated
extractionextracted with EtOAc (3×)
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-fe89ea90939c4dfdbfe428488c8a9aa7
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455521B2

Reaction notes

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