Hydrochloric Acid → HCID 66786906, compound

HRID 1015995Notes

Reaction equation

HRID 1015995 reaction equation
[OH:1][C:2]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:7][CH2:6][CH:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([NH:13]C(=O)OC(C)(C)C)[CH2:9]2)[CH2:4][CH2:3]1.[ClH:27]>O1CCOCC1>[ClH:27].[NH2:13][C@@H:10]1[CH2:11][CH2:12][N:8]([CH:5]2[CH2:6][CH2:7][C:2]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)([OH:1])[CH2:3][CH2:4]2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59556049HCID 59556049, compound

Product 1

HCID 66786906HCID 66786906, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl [(3R)-1-(4-hydroxy-4-pyridin-2-ylcyclohexyl)pyrrolidin-3-yl]carbamate (50 mg, 0.14 mmol) was added 4.0 M HCl in 1,4-dioxane (3 mL) at rt. After being stirred for 5 minutes, the product was precipitated out. To the mixture was added methanol (0.6 mL) and the solution became mostly clear with some gummy material present. The reaction was completed after 2½ hours as judged by HPLC and LCMS. This resulting mixture was concentrated to give 4-[(3R)-3-aminopyrrolidin-1-yl]-1-pyridin-2-ylcyclohexanol HCl salt (72 mg, 99%). LC/MS: 262.1 (M+H, 100%).

Workup

  1. customthe product was precipitated out
  2. additionTo the mixture was added methanol (0.6 mL)
  3. waitThe reaction was completed after 2½ hours
  4. concentrationThis resulting mixture was concentrated

Sources & evidence

ORD record
ord-6184998e2cbc4a4a8160fa716b99fcc9
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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