Triethylamine → Thiomorpholine, N-BOC protected

HRID 2215531

Reaction equation

HRID 2215531 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C(OC([O-])=O)([O:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O)=O>O1CCCC1>[N:1]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 86600350tert-Butoxycarbonyl dicarbonate

Product 1

HCID 21949316Thiomorpholine, N-BOC protectedYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiomorpholine (5.0 ml, 53 mol) was dissolved in tetrahydrofuran (200 ml); triethylamine (8.1 ml, 58 ml) was added thereto; and the reaction mixture was stirred at room temperature. tert-Butoxycarbonyl dicarbonate (13.3 ml, 58 mmol) was added thereto and the reaction mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure; and the residue was purified by silica gel column (eluent; hexane:ethyl acetate=from 80:20, 75:25 to 70:30) to yield the title compound as colorless crystals (10.4 g, 51 mmol).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 10 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customand the residue was purified by silica gel column (eluent; hexane:ethyl acetate=from 80:20, 75:25 to 70:30)

Sources & evidence

ORD record
ord-1f78b47ce5144d6ba73f778e4299dc27
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Linked notes

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