Hydrogen chloride-ethyl acetate → 2-(trimethylsilyl)ethyl (1RS,2SR)-2-aminocyclohexanecarboxylate

HRID 450764Notes

Reaction equation

HRID 450764 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])=O)(C)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[NH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:16]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 723034442-(trimethylsilyl)ethyl(1RS,2SR)-2-[(t-butoxycarbonyl)amino]cyclohexanecarboxylate

Product 1

HCID 723033142-(trimethylsilyl)ethyl (1RS,2SR)-2-aminocyclohexanecarboxylateYield 115.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.82 g of 2-(trimethylsilyl)ethyl(1RS,2SR)-2-[(t-butoxycarbonyl)amino]cyclohexanecarboxylate in 10 ml of ethyl acetate, were added 20 ml of 4 M hydrogen chloride/ethyl acetate under ice-cooling, followed by stirring at room temperature for 6 hours. The reaction solution was evaporated to obtain 2.30 g of 2-(trimethylsilyl)ethyl(1RS,2SR)-2-aminocyclohexanecarboxylate as a colorless amorphous substance.

Workup

  1. temperaturecooling
  2. customThe reaction solution was evaporated

Sources & evidence

ORD record
ord-879616591bc8486c88fa0de27a99519c
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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