Water → tert-Butyl 2-(8-(3,4-dichlorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-yloxy)ethylcarbamate

HRID 1044506Notes

Reaction equation

HRID 1044506 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:7][CH:8]1[C:17]2[CH:16]=[C:15]([OH:18])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10][CH:9]1[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.Br[CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].O>CCCCCC.CC(N(C)C)=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:7][CH:8]1[C:17]2[CH:16]=[C:15]([O:18][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10][CH:9]1[N:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 574712318-(3,4-Dichlorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 59547809tert-Butyl 2-(8-(3,4-dichlorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-yloxy)ethylcarbamateYield 97%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 31374DimethylacetamideSolvent2×

Procedure

NaH in paraffin (0.278 g, 6.38 mmol, 55% in paraffin) was washed with n-hexane and suspended in DMA (30 ml). 8-(3,4-Dichlorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-ol (1.2 g, 3.19 mmol) in DMA (20 ml) was added. After stirring for 1 h at room temperature tert-butyl 2-bromoethylcarbamate (2.14 g, 6.38 mmol) was added in portions and the mixture was stirred for 48 h. Water was added and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with saturated NaCl solution, dried over Na2SO4, and concentrated to afford a residue that was purified by flash chromatography (silica gel, MeOH/CH2Cl2 3:97). The product (1.6 g, 97%) was obtained as a yellow oil.

Workup

  1. additionwas added in portions
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford a residue that
  7. customwas purified by flash chromatography (silica gel, MeOH/CH2Cl2 3:97)

Sources & evidence

ORD record
ord-bad58d7f9b8147b8a71c4bbf8824b71e
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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