Water → 7-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-ol

HRID 2089475Notes

Reaction equation

HRID 2089475 reaction equation
[N:1]1([C:6]2[CH:15]=[C:14]3[C:9]([CH2:10][CH2:11][CH2:12][C:13]3=[O:16])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O>CO>[N:1]1([C:6]2[CH:15]=[C:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH:13]3[OH:16])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 591994477-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 675492557-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-one (0.548 g, 2.55 mmol) in methanol (20 mL) at 0° C. is added sodium borohydride (0.241 g, 3.54 mmol) and the reaction is stirred for 1.5 hours, whereupon water is added and the volatiles are removed in vacuo. The mixture is extracted with dichloromethane. The organic phase is dried over sodium sulfate, filtered, and concentrated to give 7-pyrrolidin-1-yl-3,4-dihydro-2H-naphthalen-1-ol, which is used in the next step without further purification.

Workup

  1. additionis added
  2. customthe volatiles are removed in vacuo
  3. extractionThe mixture is extracted with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-099b40a8097e4746a0f7dfce6f449449
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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