Methylamine → HCID 59556067, compound

HRID 1015981Notes

Reaction equation

HRID 1015981 reaction equation
[OH:1][C:2]1([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.CN.[CH3:23][N:24]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[OH:1][C:2]1([C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:24][CH3:23])=[O:17])=[CH:14][CH:13]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 15023906HCID 15023906, compound

Product 1

HCID 59556067HCID 59556067, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-(8-Hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)benzoic acid (560 mg, 2 mmol), methylamine (1.2 mL, 2.0 M THF solution), BOP reagent (1.07 g, 2.4 mmol) and 0.8 mL (6 mmol) of triethylamine were dissolved in 15 mL of DMF at room temperature. The reaction mixture was stirred at r.t. overnight. Direct chromatography on silica gel (flash chromatography grade) with 50% ethyl acetate-hexane gave 410 mg (70%) of the desired product: 1H NMR (CDCl3) δ 7.76 (2H, d, J=11.2 Hz), 7.56 (2H, d, J=10.9 Hz), 5.01 (H, s), 3.90 (4H, s), 3.37 (3H, s), 2.80-2.75 (2H, m), 2.60-2.45 (2H, m), 1.95-1.90 (2H, m), 1.63-1.52 (2H, m); MS: 292 (M+1)+.

Sources & evidence

ORD record
ord-7252a1f1eb6a4d3ca27df441a83aa018
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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