Tert-butyl 4-cyanopiperidine-1-carboxylate → Tert-butyl 4-cyano-4-[3-(methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate

HRID 1172704Notes

Reaction equation

HRID 1172704 reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:12]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)#[N:13].C[Si](C)(C)[N-][Si](C)(C)C.[K+]>>[C:12]([C:14]1([C:2]2[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)#[N:13]

Participants

4

Reactant 3

HCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 574300802-chloro-3-(methoxymethoxy)Pyridine

Product 1

HCID 68896415Tert-butyl 4-cyano-4-[3-(methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate

Procedure

2-Chloro-3-methoxymethoxy-pyridine (Tetrahedron 58 (2002), 309-314) (2 g, 11.5 mmol) and tert-butyl 4-cyanopiperidine-1-carboxylate (1.6 g, 7.7 mmol) were reacted in the presence of potassium hexamethyldisilazide (9.2 mmol) using the method in example 8-1 to afford the desired product: tert-Butyl 4-cyano-4-[3-(methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate: 1H NMR δ (ppm) (CDCl3): 8.21 (1H, d, J=4.6 Hz), 7.53 (1H, d, J=8.3 Hz), 7.27-7.23 (1H, m), 5.31 (2H, s), 4.20 (2H, br s), 3.55 (3H, s), 3.28 (2H, br s), 2.35 (2H, s), 2.10 (2H, br s), 1.47 (9H, s).

Sources & evidence

ORD record
ord-84114eb7bbac471ebb9d1cd03b013fbb
Source dataset
uspto-grants-2010_11
Patent number
US07834031B2

Reaction notes

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