ChemicalBook CAS DataBase List 1-(tert-butoxycarbonyl)-6-methylpiperidine-3-carboxylic acid

1-(tert-butoxycarbonyl)-6-methylpiperidine-3-carboxylic acid synthesis

4synthesis methods

Product Name:1-(tert-butoxycarbonyl)-6-methylpiperidine-3-carboxylic acid
CAS Number:1253200-91-7
Molecular formula:C12H21NO4
Molecular Weight:243.3

1009376-92-4 Synthesis

1-(tert-butyl) 3-methyl (3R,6R)-6-methylpiperidine-1,3-dicarboxylate

1009376-92-4
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1-(tert-butoxycarbonyl)-6-methylpiperidine-3-carboxylic acid

1253200-91-7
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Yield:1253200-91-7 5.41 g

Reaction Conditions:

with lithium hydroxide monohydrate in tetrahydrofuran at 20;

Steps:

15 Reference Example 15 (3R,6R)-1-(Tert-butoxycarbonyl)-6-methylpiperidine-3-carboxylic acid

Reference Example 15
(3R,6R)-1-(Tert-butoxycarbonyl)-6-methylpiperidine-3-carboxylic acid
LiOH·H₂O (1.01 g, 24.1 mmol) was added to a THF (183 mL)/H₂O (46 mL) mixed solution of methyl (3R,6R)-1-(tert-butoxycarbonyl)-6-methylpiperidine-3-carboxylate (5.9 g, 22.9 mmol), and the mixture was stirred overnight at room temperature.
H₂O was added thereto, followed by extraction with Et₂O.
Then, 2 mol/L hydrochloric acid was added to the aqueous layer, followed by extraction using EtOAc.
The obtained organic layer was dried over MgSO₄, and the desiccant was then filtered off.
The solvent was distilled off under reduced pressure to obtain the title compound (5.41 g) (colorless solid).
MS (ESI neg.) m/z: 242 [M-H]-

References:

EP2730573,2014,A1 Location in patent:Paragraph 0077-0078

tert-butyl (2R,5R)-5-(hydroxymethyl)-2-methylpiperidine-1-carboxylate

1009376-93-5
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References

24424-99-5 Synthesis

24424-99-5
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References

((3R,6R)-6-METHYLPIPERIDIN-3-YL)METHANOL

1088994-09-5
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References