Water → HCID 57554662, compound

HRID 1511859Notes

Reaction equation

HRID 1511859 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[CH2:25][CH2:24][C@@:18]3([NH:22]C(=O)[O:20][CH2:19]3)[CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O.[OH-].[Li+].O>O1CCOCC1>[NH2:22][C@:18]1([CH2:19][OH:20])[CH2:24][CH2:25][C@@H:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57554732HCID 57554732, compound

Product 1

HCID 57554662HCID 57554662, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (5R,7R)-7-(4-octyloxy-phenyl)-3-oxa-1-aza-spiro[4.4]nonan-2-one (61.0 mg, 0.177 mmol) in dioxane (3.0 mL) was treated with lithium hydroxide, hydrate (100 mg, 2.38 mmol) and water (1.0 mL). The mixture was heated to reflux for about 10 hours. The reaction was concentrated, treated with water (10 mL) and extracted twice with ether (10 mL). The ether extracts were dried over Na2SO4, filtered and concentrated. The residue was treated with 2 M HCl (2.0 mL) to yield a white solid which was collected and dried to yield 33.0 mg (52%) of [(1R,3R)-1-Amino-3-(4-octyloxy-phenyl)-cyclopentyl]-methanol; hydrochloride.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for about 10 hours
  3. concentrationThe reaction was concentrated
  4. additiontreated with water (10 mL)
  5. extractionextracted twice with ether (10 mL)
  6. dry with materialThe ether extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe residue was treated with 2 M HCl (2.0 mL)
  10. customto yield a white solid which
  11. customwas collected
  12. customdried

Sources & evidence

ORD record
ord-4f18e33d33b747aa9d077f6ad627c80e
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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