Tetrabutylammonium Fluoride → 8-(1-Hydroxy-1-(1-hydroxy-4-methyl-1,3-dihydroisobenzofuran-5-yl)-2-methylpropan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1501871Notes

Reaction equation

[Si]([O:8][CH:9]1[C:17]2[C:12](=[C:13]([CH3:41])[C:14]([CH:18]([OH:40])[C:19]([N:22]3[CH2:39][CH2:38][C:25]4([C:29](=[O:30])[N:28]([C:31]5[CH2:32][O:33][C:34](=[O:37])[C:35]=5[CH3:36])[CH2:27][CH2:26]4)[CH2:24][CH2:23]3)([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[CH2:11][O:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[OH:40][CH:18]([C:14]1[C:13]([CH3:41])=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH:9]([OH:8])[O:10][CH2:11]2)[C:19]([N:22]1[CH2:39][CH2:38][C:25]2([C:29](=[O:30])[N:28]([C:31]3[CH2:32][O:33][C:34](=[O:37])[C:35]=3[CH3:36])[CH2:27][CH2:26]2)[CH2:24][CH2:23]1)([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product of Step I (1.282 g, 2.192 mmol) in tetrahydrofuran (50 ml) was added TBAF (2.63 mL, 2.63 mmol) at 0° C., and the resulting solution was stirred at 0° C. for 2 h. After concentration, the residue was purified on TLC eluting with 10% MeOH/DCM to give the title compound. LC/MS: (M+1)+: 471.20.

Workup

concentrationAfter concentration
customthe residue was purified on TLC
washeluting with 10% MeOH/DCM

Sources & evidence

ORD record: ord-4add10cc8db14d0794669e19828db101
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206198B2

Reaction notes

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