Pyridine → HCID 18335082, compound

HRID 842223Notes

Reaction equation

HRID 842223 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH:18]([OH:20])[CH3:19])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:35](OC(=O)C)(=[O:37])[CH3:36].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C1COCC1>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH:18]([O:20][C:35](=[O:37])[CH3:36])[CH3:19])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18723463HCID 18723463, compound

Product 1

HCID 18335082HCID 18335082, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.026 g (0.057 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(1-hydroxyethyl)pyrrolidine (diastereomer 2, Example 18), 0.027 mL (0.28 mmol) of acetic anhydride, 0.046 mL of pyridine and 3.4 mg of DMAP in 2 mL of THF was stirred at rt for 18 h. The reaction mixture was concentrated and purified by chromatography (silica, hexanes:ethylacetate:(2N NH3 in MeOH), 15:15:1) to give the title compound as white solid. 1H NMR (CDCl3) δ (key peaks) 7.89-7.90 (m, 3H), 7.47-7.54 (m, 4H), 7.19 and 7.09 (d of d, 2H, J=6.0, 8.5 Hz), 6.99 and 6.94 (t, 2H, J=8.5 Hz), 5.04-5.20 (m, 1H1), 1.34 and 1.09 (d, 3H, J=6.5 Hz), Mass Spectrum (ESI) m/e=503 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by chromatography (silica, hexanes:ethylacetate:(2N NH3 in MeOH), 15:15:1)

Sources & evidence

ORD record
ord-be59071e57da4a5983c962a45a4d93c7
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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