Thiomorpholine → Tert-butyl [2-(benzylthio)-3-thiomorpholinopropyl]carbamate

HRID 1960424Notes

Reaction equation

HRID 1960424 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH:9]([S:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:10]=O)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][S:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH:9]([S:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][N:21]1[CH2:26][CH2:25][S:24][CH2:23][CH2:22]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 67164ThiomorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59136000Tert-butyl [2-(benzylthio)-3-oxopropyl]carbamate

Product 1

HCID 59135685Tert-butyl [2-(benzylthio)-3-thiomorpholinopropyl]carbamateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl[2-(benzylthio)-3-oxopropyl]carbamate (820 mg) in tetrahydrofuran (30 mL) was added thiomorpholine (0.42 mL), and the mixture was stirred at room temperature for 1 hr. Sodium triacetoxyborohydride (1.76 g) was added to the reaction mixture under ice-cooling, and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give the title compound (936 mg, yield 91%) as a colorless oil from a fraction eluted with is ethyl acetate-hexane (3:7).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c77a687666bb48a39f774dadad5feb0d
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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