Triethylamine → (9-(9-Hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

HRID 471260Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].FC(F)(F)C(O)=O.[CH3:19][C:20]1[S:24][C:23]([C:25]([N:27]2[CH2:32][C:31]3([CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[O:30][CH2:29][CH2:28]2)=[O:26])=[CH:22][CH:21]=1.C(N(CC)CC)C>CC#N>[OH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:35]1[CH2:36][CH2:37][C:31]2([O:30][CH2:29][CH2:28][N:27]([C:25]([C:23]3[S:24][C:20]([CH3:19])=[CH:21][CH:22]=3)=[O:26])[CH2:32]2)[CH2:33][CH2:34]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 9-bromo-1-nonanol (0.314 g) in MeCN (3 mL) was added to solution of (5-methylthiophen-2-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 9, step b) (0.263 g) and triethylamine (0.261 mL) in MeCN (7 mL). The resulting mixture was stirred at 60° C. under argon for 16 h. After cooling to RT the solvent was removed in vacuo. The residue was taken up in DCM, washed with brine (×2), dried over sodium sulphate, filtered and evaporated in vacuo. The white solid was purified by silica gel chromatography eluting with 0-10% MeOH in DCM to give the subtitled compound as a white solid. Yield 0.352 g.

Workup

temperatureAfter cooling to RT the solvent
customwas removed in vacuo
washwashed with brine (×2)
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated in vacuo
customThe white solid was purified by silica gel chromatography
washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record: ord-2d4d347dc2a646179d8e811deabe2cfe
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629271B2

Reaction notes

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