Azetidine → (cis)-4-Azetidin-1-yl-3-fluoro-piperidine

HRID 2066501Notes

Reaction equation

CN1CC[C:5]2([CH2:8][NH:7][CH2:6]2)CC1.C(OC([N:18]1[CH2:23][CH2:22][C:21](=O)[CH:20]([F:25])[CH2:19]1)=O)(C)(C)C.N1CCC1>>[N:7]1([C@H:21]2[CH2:22][CH2:23][NH:18][CH2:19][C@H:20]2[F:25])[CH2:8][CH2:5][CH2:6]1

Participants

Reactant 3

HCID 10422Azetidine

HCID 10560711TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

HCID 109971177-Methyl-2,7-diazaspiro[3.5]nonane

Product 1

HCID 66870306(cis)-4-Azetidin-1-yl-3-fluoro-piperidine

Procedure

Prepared according to the method used in the preparation of 7-methyl-2,7-diaza-spiro[3.5]nonane using 3-fluoro-4-oxo-piperidine-1-carboxylic acid tert-butyl ester in place of formaldehyde and azetidine in place of 2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester hydrochloride. The title compound was obtained as a colourless oil (205 mg, 56%).

Workup

customPrepared

Sources & evidence

ORD record: ord-0c43f9ad780d4c839cad79b70d40d5b2
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293735B2

Reaction notes

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