ChemicalBook CAS DataBase List (S)-tert-butyl 3-(Methoxy(Methyl)carbaMoyl)piperidine-1-carboxylate

(S)-tert-butyl 3-(Methoxy(Methyl)carbaMoyl)piperidine-1-carboxylate synthesis

2synthesis methods

Product Name:(S)-tert-butyl 3-(Methoxy(Methyl)carbaMoyl)piperidine-1-carboxylate
CAS Number:1008562-93-3
Molecular formula:C13H24N2O4
Molecular Weight:272.34

6638-79-5 Synthesis

6638-79-5
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(S)-tert-butyl 3-(Methoxy(Methyl)carbaMoyl)piperidine-1-carboxylate

1008562-93-3
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Yield:1008562-93-3 100%

Reaction Conditions:

with N-methylcyclohexylamine;chloroformic acid ethyl ester in dichloromethane at -78 - 20; for 4.25 h;

Steps:

17

To a stirring solution at -78 ⁰C under N₂ of piperidine-1 ,3-dicarboxylic acid 1-terf- butyl ester (N-BOC-(S)-nipecotic acid, 15.0 g, 65.6 mmol) and 1-methylpiperidine (9.6 ml, 79.0 mmol) in 500 ml_ of CH₂CI₂ was added rapidly (via syringe) ethyl chloroformate (6.9 mL, 72.2 mmol). The mixture (solid had formed) was stirred for 15 minutes, then solid N,O-dimethylhydroxylamine hydrochloride (7.0 g, 71.8 mmol) followed by another portion of 1-methylpiperidine (9.6 mL, 79.0 mmol) were added. The sample was allowed to slowly warm to room temperature (~4 hours), rotary evaporated, then partitioned between EtOAc and saturated NaHCO₃ solution. The organic extract was washed with sat. KH₂PO₄ and brine solutions, dried (MgSO₄), filtered and rotary evaporated to give 18.2 g (>100%) of (S)-3-(methoxy-methyl-carbamoyl)-piperidine-1-carboxylic acid, tert- butyl ester as colorless oil. MS (APCI+) m/z 173.1 [M-99, 100%]. This material was used without further purification in Preparation 18.

References:

WO2008/23258,2008,A1 Location in patent:Page/Page column 46-47

88495-54-9
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1117-97-1
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1008562-93-3
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References

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