Tetrahydrofuran → 3-Cyclohexylpropyl-(ethyl)carbamate

HRID 451766

Reaction equation

HRID 451766 reaction equation
[CH:1]1([CH2:7][C@H:8](NC(=O)OC(C)(C)C)[CH2:9]NCC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[N:31]1[C:36](=[O:37])C[CH2:34][C:32]1=O)(OCC[Si](C)(C)C)=O.C1C[O:41]CC1>>[CH:1]1([CH2:7][CH2:8][CH2:9][O:41][C:36](=[O:37])[NH:31][CH2:32][CH3:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 59201304(S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate

Product 1

HCID 1317307163-Cyclohexylpropyl-(ethyl)carbamateYield 45%

Procedure

To a solution of (S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate (338 mg) and TeocOSu (386 mg, 1.49 mmol) in THF was added TEA (0.6 mL). The resulting solution was stirred at rt for 30 min and evaporated. The residue was purified through chromatography on silica gel to give (S)-2-(trimethylsilyl)ethyl 2-(N-tert-butoxycarbonyl)amino)-3-cyclohexylpropyl-(ethyl)carbamate (287 mg, 45% over 2 steps).

Workup

  1. customevaporated
  2. customThe residue was purified through chromatography on silica gel

Sources & evidence

ORD record
ord-e0de30f8a9114fa4950dea2fb477176d
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Linked notes

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