Dichloromethane → Tert-butyl bis(2-propoxyethyl)carbamate

HRID 56172Notes

Reaction equation

HRID 56172 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][OH:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+].Br[CH2:18][CH2:19][CH3:20].C(Cl)Cl.[CH3:24][CH2:25][CH2:26]CCC>O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[CH2:18]([O:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][O:14][CH2:24][CH2:25][CH3:26])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:19][CH3:20]

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 78401-BromopropaneHCID 8058HexaneHCID 14798Sodium HydroxideHCID 4360601N-Boc-diethanolamine

Product 1

HCID 89410734Tert-butyl bis(2-propoxyethyl)carbamateYield 15%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a solution of tert-butyl bis(2-hydroxyethyl)carbamate (8.20 g, 40 mmol) in hexane (30 mL) was added a solution of NaOH (8.00 g, 200 mmol) in water (30 mL), 1-bromopropane (9.84 g, 80 mmol) and TBAB (1.00 g) under N2. The reaction mixture was refluxed overnight, then cooled to rt and poured into CH2Cl2 (100 mL). The organic phase was washed with water (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as colorless oil (1.78 g, 15%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. washThe organic phase was washed with water (100 mL×3)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

Sources & evidence

ORD record
ord-d6f66929b1a14e1a90afd6ed4dd0b0e3
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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