Trifluoroacetic acid → 2-Oxa-7-azaspiro[3.5]nonane 2,2,2-trifluoroacetate

HRID 2095493Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:23][CH2:22][C:18]2([CH2:21][O:20][CH2:19]2)[CH2:17][CH2:16]1)=O)(C)(C)C>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:19]1[C:18]2([CH2:22][CH2:23][NH:15][CH2:16][CH2:17]2)[CH2:21][O:20]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 219552107-Boc-2-oxa-7-azaspiro[3.5]nonane

Product 1

HCID 670747192-Oxa-7-azaspiro[3.5]nonane 2,2,2-trifluoroacetate

Procedure

Trifluoroacetic acid (125 mg, 1.1 mmol) was added at 0° C. to a solution of 2-oxa-7-azaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester (U.S. Pat. No. 7,105,507 B2; 50 mg, 0.22 mmol) in dichloromethane, then after 1 h the reaction mixture was concentrated to afford the title compound (83 mg), which contained approximately one additional equivalent of trifluoroacetic acid. Colorless oil, 1H-NMR (300 MHz, DMSO-d6): 8.4 (br. s, 2H), 4.32 (s, 4H), 3.05-2.95 (m, 4H), 1.95-1.9 (m, 4H).

Workup

concentration50 mg, 0.22 mmol) in dichloromethane, then after 1 h the reaction mixture was concentrated

Sources & evidence

ORD record: ord-49bdfbbc4aa54c658ab41d5d2623c823
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445674B2

Reaction notes

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