Hydrochloric Acid → HCID 67070408, compound

HRID 602103Notes

Reaction equation

HRID 602103 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH:16][C@H:17]3[C@H:21]([OH:22])[CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][C@H:17]3[C@H:21]([OH:22])[CH2:20][NH:19][CH2:18]3)=[O:15])=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131728747HCID 131728747, compound

Product 1

HCID 67070408HCID 67070408, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of trans-tert-butyl 3-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)-4-hydroxypyrrolidine-1-carboxylate (500 mg, 1.24 mmol) in dioxane was added 4N HCl in dioxane (10 mL). The reaction was stirred at room temperature for ˜4 hrs and then diluted with ether to give a white solid, which was filtered and collected to give the desired product as the hydrochloride salt, trans-6-(3-fluorophenyl)-N-[4-hydroxypyrrolidin-3-yl]nicotinamide (390 mg, 92% ). LC/MS (M+H)=301.9 observed, 302.13 expected.

Workup

  1. customto give a white solid, which
  2. filtrationwas filtered
  3. customcollected

Sources & evidence

ORD record
ord-3263f63b852f403098777fa25b1eeb33
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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