Ammonium Hydroxide → tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

HRID 271294Notes

Reaction equation

HRID 271294 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([O:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+:16].[OH-]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]([CH2:12][NH2:16])([OH:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate2×

Product 1

HCID 23396319tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Aminomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester is prepared from 1-oxa-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester (Bourrain et al Bioorg. Med. Chem. Lett. 9(23):3369-3374 (1999)). Concentrated aqueous NH4OH (6 mL) is added to a solution of 1-oxa-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester (0.50 g, 2.3 mmol) in MeOH (4 mL) at 0° C. The reaction mixture is removed from the cooling and allowed to warm to room temperature. After 7 hours, the reaction mixture is concentrated under reduced pressure to afford desired product as a white solid.

Workup

  1. customThe reaction mixture is removed from the cooling and
  2. concentrationthe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ad92af1b34e4710b4fc0c8ae0e5058d
Source dataset
uspto-grants-2008_11
Patent number
US07452895B2

Reaction notes

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