Ammonium Hydroxide → (1S)-6-Oxaspiro[2.5]octane-1-carboxamide

HRID 656248Notes

Reaction equation

HRID 656248 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[C@@H:13]1([C:21]([OH:23])=O)[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:14]1.[OH-].[NH4+]>C(OCC)(=O)C>[C@@H:13]1([C:21]([NH2:3])=[O:23])[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:14]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 57429840HCID 57429840, compound

Product 1

HCID 57429839(1S)-6-Oxaspiro[2.5]octane-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

18.85 g of carbonyldiimidazole are added to a solution of 17.66 g of (S)-6-oxaspiro[2.5]-octane-1-carboxylic acid (prepared in analogy to building block FFFFa from (R)-4-benzyl-3-((S)-6-oxaspiro[2.5]-octane-1-carbonyl)oxazolidin-2-one (building block FFFFb)) in 330 ml of ethyl acetate. The reaction solution is left to stand at room temperature for 6 hours and then 330 ml of 25% ammonium hydroxide solution are added. The reaction mixture is stirred at room temperature for 16 hours, the phases are separated, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water until neutral, dried with sodium sulphate and evaporated. The title compound is obtained from the residue by flash chromatography (SiO2 60 F) as a yellowish oil which may crystallize if sufficiently pure. Rf=0.28 (dichloromethane-methanol-conc. ammonia 25% 200:20:1).

Workup

  1. waitThe reaction solution is left
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washThe combined organic phases are washed with water until neutral,
  5. dry with materialdried with sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-d9eb3787e12c4fa798c94bc4e7e7846b
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

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