Dimethylamine → (2R)-2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)-N,N-dimethylacetamide

HRID 1433170Notes

Reaction equation

[OH:1][C:2]1([C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:9](O)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:38]([CH3:40])[CH3:39])C2C=CC=CC=2N=N1.CNC>C(Cl)Cl>[OH:1][C:2]1([C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:9]([N:38]([CH3:40])[CH3:39])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (2R)-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)acetic acid (156 mg, 0.59 mmol) in methylene chloride (1 mL) was treated with benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (313 mg, 0.71 mmol) and dimethylamine (2.0 M in tetrahydrofuran, 1.5 mL, 2.95 mmol). The reaction was stirred at 25° C. for 1.5 h after which time the solvent was evaporated and the product was purified via Biotage™ Horizon chromatography (FLASH 25 M, silica, gradient from 5% ethyl acetate/hexane to 36% ethyl acetate/hexane over 650 mL) to yield 160 mg (93%) (2R)-2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)-N,N-dimethylacetamide as a white solid. MS (ESI) m/z 292; [α]D25=+81° (c=0.010 g/mL, EtOH).

Workup

customwas evaporated
customthe product was purified via Biotage™ Horizon chromatography (FLASH 25 M, silica, gradient from 5% ethyl acetate/hexane to 36% ethyl acetate/hexane over 650 mL)

Sources & evidence

ORD record: ord-f34f03231fb741bf88fbecbe60607ede
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612210B2

Reaction notes

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