Sodium Hydroxide → HCID 57471419, compound

HRID 510545Notes

Reaction equation

HRID 510545 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16]C)[CH:14]=2)[CH2:9][CH2:8][CH:7]1[N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([OH:16])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57467339HCID 57467339, compound

Product 1

HCID 57471419HCID 57471419, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(1-(3-Chlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidine (6.6 g, 18.54 mmol) was dissolved in dichloromethane (100 mL). A 1 M solution of bortribromide in dichloromethane (55.6 mL, 55.6 mmol) was added dropwise under cooling maintaining the reaction mixture at room temperature. The reaction mixture was stirred at room temperature for 2 h. The reaction was poured on ice, made alkaline with sodium hydroxide. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were washed successively with sodium bicarbonate and brine. The combined extracts were dried (MgSO4) and the solvent was evaporated in vacuo. The crude product (5.5 g) was used for the next step without further purification.

Workup

  1. temperatureunder cooling
  2. additionThe reaction was poured on ice
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed successively with sodium bicarbonate and brine
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent was evaporated in vacuo
  7. customThe crude product (5.5 g) was used for the next step without further purification

Sources & evidence

ORD record
ord-879561223c5e4280973ab785e764e9c3
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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