Hydrochloric Acid → HCID 68906848, compound

HRID 2110364Notes

Reaction equation

HRID 2110364 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 68905000HCID 68905000, compound

Product 1

HCID 68906848HCID 68906848, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-2-[2-(S)-(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 hydrochloric acid (1.0 mL, 1.0 mmol) was added. After 16 hours the mixture was concentrated and purified via flash column chromatography (silica, 10% methanol saturated with ammonia in chloroform) to give 19 mg (50%) (1R,2S)-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 1 N ethereal solution of hydrochloric acid (0.06 mL, 0.06 mmol, 1 equivalent). The white precipitate was collected and dried under vacuum to give 17 mg of (1R,2S)-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]+), 325.1711

Workup

  1. concentrationAfter 16 hours the mixture was concentrated
  2. custompurified via flash column chromatography (silica, 10% methanol saturated with ammonia in chloroform)

Sources & evidence

ORD record
ord-c0c39e3bd7074d809cd619f5f5f8d5e2
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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