Hydrochloric Acid → HCID 88014372, compound

HRID 365909Notes

Reaction equation

HRID 365909 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([O:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2C(OC(C)(C)C)=O)[CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=[CH2:3].[ClH:25].O.CO>CCOCC>[ClH:10].[ClH:25].[CH2:1]([C:4]1[CH:5]=[C:6]([O:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)[CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 962WaterHCID 22961883HCID 22961883, compound

Product 1

HCID 88014372HCID 88014372, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-allyl-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)6-chloropyridine in Et2O was added hydrogen chloride (4.0 M in 1,4-dioxane) carefully to afford the tittle compound: mp 90-92° C.; 1H NMR (D2O) δ 1.92 (m, 1H), 2.02-2.20 (m, 2H), 2.27 (m, 1H), 3.40 (t, 2H, J=7.0 Hz), 3.49 (d, 2H, J=6.5 Hz), 4.11 (m, 1H), 4.21 (dd, 1H, J=7.5, 10.5 Hz), 4.43 (dd, 1H, J=3.5, 10.5 Hz), 5.10 (dd, 1H, J=1.5, 17.0 Hz), 5.18 (dd, 1H, J=2.0, 10.0 Hz), 6.03 (m, 1H), 7.44 (d, 1H, J=3.0 Hz), 7.98 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 253 (M+H)+. Anal. Calcd for C13H17ClN2O.2 HCl.0.8 H2O: C, 45.91; H, 6.11; N, 8.24. Found: C, 45.90; H, 6.36; N, 8.20. [α]25D -11.2 (c 1.4, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-a3b64b38ab0a4cfbaf6f95c1d4954dac
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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