Formaldehyde → HCID 86605495, compound

HRID 2103053Notes

Reaction equation

HRID 2103053 reaction equation
[C:1]([C:5]1[CH:17]=[C:16]2[C:8]([CH2:9][CH2:10][C:11]3([O:15]2)[CH2:14][CH2:13][CH2:12]3)=[CH:7][C:6]=1[OH:18])([CH3:4])([CH3:3])[CH3:2].[CH2:19]=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>O1CCOCC1>[C:1]([C:5]1[CH:17]=[C:16]2[C:8]([CH2:9][CH2:10][C:11]3([O:15]2)[CH2:14][CH2:13][CH2:12]3)=[C:7]([CH2:19][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:6]=1[OH:18])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 86605496HCID 86605496, compound

Product 1

HCID 86605495HCID 86605495, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 7-tert-butylspiro[chroman-2,1′-cyclobutan]-6-ol (2.8 g) in dioxane (5 mL) was added an aqueous formaldehyde solution (3.7 mL, 37% in H2O) followed by morpholine (4.0 mL). The reaction was stirred under argon at 90° C. for 2.5 hours, cooled in an ice bath with stirring to precipitate product which was filtered off as a white solid, washed with H20, and air dried to give 7-tert-butyl-5-(morpholinomethyl)spiro[chroman-2,1′-cyclobutan]-6-ol (2.45 g). 1H-NMR (300 MHz, CDCl3) δ=10.74 (s, 1H), 6.73 (s, 1H), 3.77 (br s, 4H), 3.68 (s, 2H), 2.67-2.63 (t, 2H), 2.59 (br s, 4H), 2.29-2.24 (m, 2H), 2.08-1.94 (m, 5H), 1.70-1.65 (m, 1H), 1.40 (s, 9H) ppm. 13C-NMR (75 MHz, CDCl3) δ=150.32, 145.73, 136.19, 118.32, 117.55, 115.00, 76.22, 66.81, 56.78, 52.69, 34.60, 33.91, 29.53, 20.01, 12.46 ppm. MS (m/z)=346 (M+H+), 259 [M-morpholine+H+].

Workup

  1. temperaturecooled in an ice bath
  2. stirringwith stirring
  3. customto precipitate product which
  4. filtrationwas filtered off as a white solid
  5. washwashed with H20, and air
  6. customdried

Sources & evidence

ORD record
ord-5d3a73ae18e942b0848a7dee2475d1b3
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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