Hydrochloric Acid → Hydrate;hydrochloride

HRID 1511853Notes

Reaction equation

HRID 1511853 reaction equation
[NH2:1][C@:2]1([C:21](OC)=[O:22])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:9][CH:8]=2)[CH2:3]1.[BH4-].[Na+].[ClH:27]>CCO>[NH2:1][C@:2]1([CH2:21][OH:22])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:9][CH:8]=2)[CH2:3]1.[OH2:19].[ClH:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57554704(1R,3R)-methyl 1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentanecarboxylate

Product 2

HCID 21885828Hydrate;hydrochlorideHCID 25001810((1R,3R)-1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of (1R,3R)-methyl 1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentanecarboxylate (12.84 g, 38.5 mmol) in EtOH (50 mL) was added dropwise to a solution of sodium borohydride (4.37 g, 115 mmol) in EtOH (50 mL). After about 15 hours 2N HCl was added slowly to the reaction mixture. The mixture was partially concentrated in vacuo and partitioned between EtOAc and water. The organic layer was separated and the solvent was removed in vacuo and the residue was dissolved in warm dioxane (100 mL) and water (1 mL) after cooling to about room temperature. The resulting solid was collected by filtration and dried in vacuo to provide ((1R,3R)-1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentyl)methanol, hydrochloric acid, monohydrate.

Workup

  1. concentrationThe mixture was partially concentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. customthe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in warm dioxane (100 mL)
  6. temperaturewater (1 mL) after cooling to about room temperature
  7. filtrationThe resulting solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-3b8a2d847be54882ae328e47c6508082
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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