Sodium hydride → HCID 71245505, compound

HRID 532132Notes

Reaction equation

HRID 532132 reaction equation
[H-].[Na+].[CH2:3]([CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=2)[O:13][CH2:12][CH:11]1[NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:28][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].C(=O)([O-])O.[Na+]>CC(N(C)C)=O>[CH2:24]([O:23][C:22](=[O:26])[NH:21][CH:11]1[CH:10]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:28][CH2:29][NH:30][C:31]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:37])[CH:18]=2)[O:13][CH2:12]1)[CH3:25]

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 516892Sodium BicarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate2×HCID 71245529HCID 71245529, compound

Product 1

HCID 71245505HCID 71245505, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

150 mg (3.75 mmol, 60% in mineral oil) of sodium hydride were suspended under nitrogen atmosphere in 2 m dry dimethyl acetamide. 488 mg (1.5 mmol) of ethyl 4-benzyl-6-hydroxychroman-3-ylcarbamate dissolved in 8 ml dry dimethyl acetamide were added dropwise at room temperature and stirred for 1 h. Then 1.0 g (4.47 mmol) of tert-butyl 2-bromoethylcarbamate dissolved in 2 ml acetate amide were added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 84 h. Then additional 50 mg (1.4 mmol) sodium hydride were added and the mixture was stirred for 30 min before additional 350 mg of tert-butyl 2-bromoethylcarbamate were added and the mixture was stirred for additional 72 h. The reaction mixture was poured onto diluted sodium hydrogencarbonate solution and extracted with ether (2×). The combined organic phases were washed with water (2×), dried over MgSO4 and concentrated (1.5 g of crude). The crude material was purified by flash chromatography to give 587 mg (1.25 mmol, 84%) of the desired product.

Workup

  1. additionwere added dropwise at room temperature
  2. additionwere added slowly
  3. stirringstirred for 84 h
  4. additionwere added
  5. stirringthe mixture was stirred for additional 72 h
  6. extractionextracted with ether (2×)
  7. washThe combined organic phases were washed with water (2×)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated (1.5 g of crude)
  10. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-2202d64dc03e483899dd51be794e22c2
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

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