Formaldehyde → N-benzyl-6-(benzyloxy)-N-methylhexahydrofuro[3,2-b]furan-3-amine

HRID 1053911Notes

Reaction equation

[CH2:1]([NH:8][CH:9]1[CH2:13][O:12][CH:11]2[CH:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][O:16][CH:10]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]=O>C(O)=O>[CH2:1]([N:8]([CH3:25])[CH:9]1[CH2:13][O:12][CH:11]2[CH:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][O:16][CH:10]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of N-benzyl-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-amine (9.88 g, 30.36 mmol) in HCOOH (19 mL) was added formalin (2.96 g, 36.43 mmol). After addition, the reaction mixture was stirred at 110° C. overnight and concentrated in vacuo. The residue was adjusted to pH=8 with a saturated Na2CO3 solution and extracted with EtOAc (100 mL×3). The combined organic phases were washed with water (100 mL×3) followed by brine (100 mL), then dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2) to give the title compound as yellow oil (4.77 g, 46.4%).

Workup

additionAfter addition
concentrationconcentrated in vacuo
extractionextracted with EtOAc (100 mL×3)
washThe combined organic phases were washed with water (100 mL×3)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2)

Sources & evidence

ORD record: ord-c81cb7519c1346168f3036a692bd2ae1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394281B2

Reaction notes

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