Triethylamine → 4-(t-Butoxycarbonyl)-3-(pyrrolidine-1-carbonyl)thiomorpholine

HRID 326753Notes

Reaction equation

HRID 326753 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][S:23][CH2:22][CH:21]1[C:26](O)=[O:27])=[O:19])([CH3:16])([CH3:15])[CH3:14].P(C#N)([O-])(OCC)=O>O1CCCC1.O>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][S:23][CH2:22][CH:21]1[C:26]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:27])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 27568314-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acidHCID 86180093Ethyl cyanophosphate

Product 1

HCID 157301454-(t-Butoxycarbonyl)-3-(pyrrolidine-1-carbonyl)thiomorpholineYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Triethylamine (3.1 ml), followed by a solution of pyrrolidine (2.0 ml) in 10 ml of tetrahydrofuran, was added at 0° C. under a stream of nitrogen to a solution of 5.0 g of 4-(t-butoxycarbonyl)thiomorpholine3-carboxylic acid in 100 ml of tetrahydrofuran. After the mixture had been stirred for 1 hour, a solution of 3.6 g of ethyl cyanophosphate in 10 ml of tetrahydrofuran was added to the mixture and the mixture was stirred for 5 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to yield 4.61 g (74%) of 4-(t-butoxycarbonyl)-3-(pyrrolidine-1-carbonyl)thiomorpholine.

Workup

  1. stirringthe mixture was stirred for 5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bf509a1480514a31bae5d06696ba1bd3
Source dataset
uspto-grants-1993_12
Patent number
US05270327

Reaction notes

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