Hydrochloric Acid → HCID 68903026, compound

HRID 2110362Notes

Reaction equation

HRID 2110362 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@H:13]([OH:31])[C@@H:14]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1)[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=O)(C)(C)C.Cl>CO>[F:30][C:26]1[CH:25]=[C:24]([C@@H:14]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)[C@H:13]([C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[OH:31])[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68902902HCID 68902902, compound

Product 1

HCID 68903026HCID 68903026, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-[2-(R)-(3-Fluoro-phenyl)-1-hydroxy-2-indol-1-yl-ethyl]-(S)-pyrrolidine-1-carboxylic acid tert-butyl ester (50 mg, 0.12 mmol) was dissolved in methanol (1 mL) and a 1N ethereal solution of hydrochloric acid (0.96 mL, 0.96 mmol) was added. After 6 hours the mixture was concentrated and purified via flash column chromatography (silica, 10% methanol saturated with ammonia in chloroform) to give 6 mg (15%) (1S,2R)-2-(3-fluorophenyl)-2-(1H-indol-1-yl)-1-[(2S)-pyrrolidin-2-yl]ethanol. The freebase was dissolved in diethyl ether (2 mL) and treated with a 1N ethereal solution of hydrochloric acid (0.02 mL, 0.02 mmol, 1 equivalent). The white precipitate was collected and dried under vacuum to give 4 mg of (1S,2R)-2-(3-fluorophenyl)-2-(1H-indol-1-yl)-1-[(2S)-pyrrolidin-2-yl]ethanol hydrochloride. HRMS: calcd for C20H21FN2O+H+, 325.17107; found (ESI, [M+H]+), 325.1712

Workup

  1. concentrationAfter 6 hours the mixture was concentrated
  2. custompurified via flash column chromatography (silica, 10% methanol saturated with ammonia in chloroform)

Sources & evidence

ORD record
ord-4783965742154255b7c48e2ffeaf4013
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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