Triethylamine → Thiomorpholine, N-BOC protected

HRID 2376855

Reaction equation

HRID 2376855 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 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Thiomorpholine (5.0 ml, 53 mmol) was dissolved in tetrahydrofuran (200 ml); triethylamine (8.1 ml, 58 mmol) 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-1291f0e48b6f454687c05243ca8ecd72
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Linked notes

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