Ammonium Hydroxide → 4-(Aminomethyl)oxan-4-ol

HRID 271295

Reaction equation

HRID 271295 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:2]1.[NH4+:9].[OH-]>CO>[NH2:9][CH2:2][C:3]1([OH:1])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1604391,6-Dioxaspiro[2.5]octane2×

Product 1

HCID 436087544-(Aminomethyl)oxan-4-olYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Aminomethyl-tetrahydro-pyran-4-ol is prepared from 1,6-dioxa-spiro[2.5]octane. A MeOH (3.5 mL) solution of 1,6-dioxa-spiro[2.5]octane (0.19 g, 1.7 mmol) is added to concentrated aqueous NH4OH (4.3 mL) at 0° C. The reaction mixture is warmed to room temperature and stirred for 16 hours. The reaction mixture is concentrated under reduced pressure and purified by column chromatography (10% MeOH, 2% Et3N in DCM) to afford 90 mg (41%) of the desired product as a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. custompurified by column chromatography (10% MeOH, 2% Et3N in DCM)

Sources & evidence

ORD record
ord-567b4bd2d8b54962a35216971f430169
Source dataset
uspto-grants-2008_11
Patent number
US07452895B2

Linked notes

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