Morpholine → 1,1-Dimethylethyl 4-hydroxy-4-(4-morpholinylmethyl)-1-piperidinecarboxylate

HRID 253025Notes

Reaction equation

HRID 253025 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].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]([OH:13])([CH2:12][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Product 1

HCID 583931721,1-Dimethylethyl 4-hydroxy-4-(4-morpholinylmethyl)-1-piperidinecarboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Oxa-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester (100 mg, 0.47 mmol) and morpholine (42 μL, 0.48 mmol, 1.03 eq) were stirred in EtOH at RT overnight. Solvent was removed in vacuo and the residue purified by flash chromatography (silica gel, 4% MeOH/DCM) to give 4-hydroxy-4-morpholin-4-ylmethyl-piperidine-1-carboxylic acid tert-butyl ester as a white solid (91.4 mg, 67%).

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue purified by flash chromatography (silica gel, 4% MeOH/DCM)

Sources & evidence

ORD record
ord-1e21c89e02ed47edbf2f4bdbe6a94fec
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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