Methanol → Tert-butyl 4-((ethylamino)methyl)-4-hydroxypiperidine-1-carboxylate

HRID 1525930Notes

Reaction equation

HRID 1525930 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.[CH2:16]([NH2:18])[CH3:17].CO>>[CH2:16]([NH:18][CH2:2][C:3]1([OH:1])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)[CH3:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 6341EthylamineHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Product 1

HCID 39359816Tert-butyl 4-((ethylamino)methyl)-4-hydroxypiperidine-1-carboxylate

Conditions

Temperature
100 °C

Procedure

Into a 100 mL round bottom flask was placed tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (2 g, 9.38 mmol). To this was added 2M ethanamine in methanol (23.44 ml, 46.9 mmol). A condenser was attached to the flask and the solution was stirred at reflux (100° C.) overnight. The solution was cooled and concentrated in vacuo to afford the title compound (2.4 g) which was carried forward without further purification. MS(ES)+ m/e 259.1 [M+H]+.

Workup

  1. customInto a 100 mL round bottom flask was placed
  2. customA condenser was attached to the flask
  3. temperatureThe solution was cooled
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-837aa4d0c1834182be716f3b835dfd0a
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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