Hydrochloric Acid → HCID 10269002, compound

HRID 1280723Notes

Reaction equation

HRID 1280723 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16](=[O:24])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:10]2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>CO>[OH:24][CH:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][CH:9]([S:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 18425759HCID 18425759, compound

Product 1

HCID 10269002HCID 10269002, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(RS)-4-[3-(4-Hydroxy-phenylsulfanyl)-pyrrolidin-1-yl]-1-phenyl-butan-2-one (200 mg, 0.6 mmol) in MeOH (3 ml) was treated with NaBH4 (33.2 mg, 0.9 mmol). After 15 minutes stirring at room temperature, the reaction mixture was acidified to pH 3 with 1N HCl then adjusted to pH 8 with saturated NaHCO3. The aqueous phase was extracted with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered and the solvent was evaporated. The residue was chromatographed over silica gel (ethylacetate) to provide (3RS, 3RS) and (3RS,3SR)-4-[1-(3-hydroxy-4-phenyl-butyl)-pyrrolidin-3-ylsulfanyl]-phenol (187 mg, 93%) as a white foam, MS: m/e=344.3 (M+H+).

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed over silica gel (ethylacetate)

Sources & evidence

ORD record
ord-0203ff2884614faaa58e2d164648881d
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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