Triethylamine → (RS)-4-[1-(4-phenyl-butyl)-pyrrolidine-3-sulfonyl]-phenol hydrochloride

HRID 1280694Notes

Reaction equation

HRID 1280694 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:12][CH2:11][CH:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:9]1.[C:23]1([CH2:29][CH2:30][CH2:31][CH:32]=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:55].CCOCC>ClCCCl.CO>[ClH:55].[C:23]1([CH2:29][CH2:30][CH2:31][CH2:32][N:8]2[CH2:12][CH2:11][CH:10]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:9]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 290304-PhenylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 10953452Ether hydrochlorideHCID 18425771(RS)-4-(Pyrrolidine-3-sulfonyl)-phenol trifluoroacetic acid

Product 1

HCID 18425851(RS)-4-[1-(4-phenyl-butyl)-pyrrolidine-3-sulfonyl]-phenol hydrochlorideYield 70%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

(RS)-4-(Pyrrolidine-3-sulfonyl)-phenol trifluoroacetic acid salt (0.22 g, 0.65 mmol), 4-phenyl-butyraldehyde (0.096 g, 0.65 mmol), triethylamine (0.090 ml., 0.65 mmol), and sodium triacetoxyborohydride (0.2 g, 0.97 mmol) were suspended in 1,2-dichloroethane (4 ml). After 3 hours stirring at room temperature, the reaction mixture was quenched with saturated NaHCO3 (10 ml). The aqueous phase was extracted with CH2Cl2 (3 times). The combined organic phases were dried over Na2SO4, filtered and the solvent was evaporated. The residue was chromatographed over silica gel (CH2Cl2—MeOH, 19:1) to provide a white solid which was suspensed in MeOH. HCl-Et2O was added to provide (RS)-4-[1-(4-phenyl-butyl)-pyrrolidine-3-sulfonyl]-phenol hydrochloride (0.180 g, 70%) as a white solid, m.p. 121-124° C. and MS: m/e=360.3 (M+H+).

Workup

  1. customthe reaction mixture was quenched with saturated NaHCO3 (10 ml)
  2. extractionThe aqueous phase was extracted with CH2Cl2 (3 times)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was chromatographed over silica gel (CH2Cl2—MeOH, 19:1)
  7. customto provide a white solid which

Sources & evidence

ORD record
ord-45cd2748bfe344a5a08e08e4b7f1299e
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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