2-Amino-1-butanol → HCID 16659476, compound

HRID 990950Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH3:12][CH2:13][CH:14]([NH2:17])[CH2:15][OH:16].C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH:17][C@H:14]([CH2:13][CH3:12])[CH2:15][OH:16]

Participants

Conditions

Temperature: 90 °C

Procedure

This compound was prepared according to General Method 18 (EXAMPLE 45) from 3,4-difluoronitrobenzene (5.34 mL, 0.048 mol), R-(−)-2 amino-1-butanol (4.14 mL, 0.044 mol) and sodium bicarbonate (3.68 g, 0.044 mol) in 133 mL anhydrous DMF heated at 90° C. for 12 hrs to afford 9.9 g (99%) of (2R)-2-(2-fluoro-4-nitrophenyl)amino-1-butanol, a yellow oil, after flash chromatography (gradient elution, hexanes:ethyl acetate 95:5 to 50:50). Data for (2R)-2-(2-fluoro-4-nitrophenyl)amino-1-butanol: 1H NMR (500 MHz, CDCl3) δ 7.98 (dd, J=8.8, 1.5, 1H), 7.89 (dd, J=11.7, 2.4, 1H), 6.71 (dd, J=8.8, 8.8, 1H), 4.72 (bs, 1H), 3.81 (m, 1H), 3.73 (m, 1H), 3.55 (m, 1H), 1.76 (m, 1H), 1.63 (m, 1H), 1.02 (t, J=7.8, 3H).

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-9b4f28210abb44ad97aea03ffc93bb31
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462038B1

Reaction notes

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