HCID 11652012, compound → HCID 11521945, compound

HRID 1296221Notes

Reaction equation

HRID 1296221 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH2:17])=[O:16])[OH:11])[CH3:3]>C(#N)C>[CH3:3][N:2]([CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@@:6]1([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH2:17])=[O:16])[OH:11])[CH3:1]

Participants

3

Reactant 1

HCID 11652012HCID 11652012, compound

Product 1

HCID 11521945HCID 11521945, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 3-[(1-RS,2RS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide was then resolved using a Chiralpak AD column with 100% acetonitrile as the eluent and with 100% ethanol for rinsing the column in between each injection, to afford (−)-3-[(1R,2R)-rel-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide (2.25 g): MS m/z 277.0 (MH+); [α]D25 −33.5 (c 1, CHCl3); Analytical reverse phase HPLC (gradient 10-90% MeCN, 0.1% aqueous TFA) tR=1.52 min, ˜99%; 1H NMR (CDCl3) δ 1.35-1.43 (s, 1H), 1.55-1.65 (m, 2H), 1.66-1.68 (m, 3H), 1.74-1.79 (m, 1H), 1.88 (d, 1H, J=13 Hz), 2.02-2.05 (m, 3H), 2.18 (s, 6H), 2.43-2.46 (m 1H), 5.69 (s, 1H), 6.44 (s, 1H), 7.43 (t, 1H, J=7.7 Hz), 7.69-7.72 (m, 2H), 8.0 (s, 1H).

Workup

  1. washwith 100% ethanol for rinsing the column in between each injection

Sources & evidence

ORD record
ord-8f78fa8a7c4b4082abf61bfe7e200974
Source dataset
uspto-grants-2007_07
Patent number
US07244866B2

Reaction notes

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