Sodium hydride → Benzyl 4-(2-hydroxyethyl)-3-oxopiperazine-1-carboxylate

HRID 2291019Notes

Reaction equation

HRID 2291019 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[H-].[Na+].Br[CH2:21][CH2:22][O:23]C1CCCCO1>CN(C)C=O>[C:1]([N:11]1[CH2:16][CH2:15][N:14]([CH2:21][CH2:22][OH:23])[C:13](=[O:17])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 736777Benzyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 53766777Benzyl 4-(2-hydroxyethyl)-3-oxopiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-carbobenzoxypiperazin-3-one (234 mg, 1.0 mmol) in dimethylformamide (10 ml) under nitrogen was added in one portion, 50% sodium hydride (48 mg, 1 mmol). After stirring at 20°-25° for 30 minutes until all of the sodium hydride had reacted, a solution of 2-(2-bromoethoxy)-tetrahydropyran (209 mg, 1 mmol) in dimethylformamide (2 ml) was added and the reaction mixture stirred at 20°-25° for 20 hours. Solvent was removed at 40°-45° and 0.1 mm and the residue chromatographed over silica gel. Elution with 2% isopropanol -98% methylene chloride gave the pure protected alcohol as an oil.

Workup

  1. customhad reacted
  2. customSolvent was removed at 40°-45°
  3. custom0.1 mm and the residue chromatographed over silica gel
  4. washElution with 2% isopropanol -98% methylene chloride

Sources & evidence

ORD record
ord-8e39b328b3f04ef38d38be2557666d65
Source dataset
uspto-grants-1986_10
Patent number
US04619927

Reaction notes

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