Water → 2-Benzyloxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane

HRID 77339

Reaction equation

[OH:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)[O:4]1.[H-].[Na+].[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:23]([O:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH2:8][CH2:9][N:10]([CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11][CH2:12]2)[O:4]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 58 °C

Procedure

2-hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane (compound 1, 50 gm, 0.18 mole) was dissolved in toluene (250 ml) at room temperature. 10 gm of 60% of sodium hydride in toluene (300 ml) was added to the above solution until the effervescence ceased. 2 gram of phase transfer catalyst tetrabutylammonium bromide (TBAB) was added. Benzyl chloride, 23 gm was then added drop wise to the above reaction mass and the reaction was maintained at 58° C. for 15 hrs. The reaction mass was poured into water and organic layer was separated. Toluene was removed under reduced pressure to get a thick reddish brown liquid. The yield is 84%.

Workup

customwas separated
customToluene was removed under reduced pressure
customto get a thick reddish brown liquid

Sources & evidence

ORD record: ord-a24ceebfe54e4f4bba2988ebc1183c6b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841296B2

Linked notes

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