1-Chloromethylnaphthalene → HCID 19382446, compound

HRID 327783Notes

Reaction equation

HRID 327783 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl[CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>CS(C)=O>[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][CH:12]([O:15][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 19382446HCID 19382446, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.27 g of an 80% strength suspension of sodium hydride in paraffin (44 mmol) were added in small portions at 0° C. to a solution of 7.49 g (40 mmol) of 1-tert.butoxycarbonyl-3-hydroxy-pyrrolidine in 40 ml of dry dimethyl sulphoxide. 7.77 g (44 mmol) of 1-chloromethyl-naphthalene were subsequently slowly added dropwise. After 3 hours at room temperature, the mixture was poured into 200 ml of saturated ammonium chloride solution, extracted a number of times using ether, dried (MgSO4) and concentrated. Flash chromatography (petroleum ether-toluene, then toluene-ethyl acetate gradients) gave 10.5 g of the title compound (76%) as a yellowish oil.

Workup

  1. extractionextracted a number of times
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bf8338795def4920899056d5e9672210
Source dataset
uspto-grants-1993_12
Patent number
US05274097

Reaction notes

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