Dimethylamine → HCID 11673337, compound

HRID 2103019Notes

Reaction equation

HRID 2103019 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:17].C=O.[CH3:21]NC.O.Cl.[BH4-].[Na+]>CO>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:7]1([CH2:8][CH2:9][CH2:10]1)[CH:6]([CH3:21])[C:5]2=[O:17]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 21885828Hydrate;hydrochlorideHCID 69059851HCID 69059851, compound

Product 1

HCID 11673337HCID 11673337, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-hydroxy-5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one (220 mg), formaldehyde (1 mL, 37% in water), dimethylamine solution (1 mL, 2.0 M in methanol), and concentrated HCl water solution (0.1, mL) was heated by microwave to 150° C. for 10 min. The allyl intermediate was treated with excessive NaBH4 in methanol at room temperature to give 6-hydroxy-3,5,7,8-tetramethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one, which was purified by chromatography (silica gel, hexane-ethyl acetate 3%).

Sources & evidence

ORD record
ord-6a10801f203644ad85595b44f0da303f
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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