Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → Tert-butyl 4-(2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)piperidine-1-carboxylate

HRID 1778067Notes

Reaction equation

HRID 1778067 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][C:5]=1[CH:14]1[CH2:19]COC[CH2:15]1.CC1(C)C(C)(C)OB(C2C[CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32]C=2)O1>>[CH3:1][O:2][CH:3]([O:20][CH3:21])[C:4]1[C:5]([CH:14]2[CH2:19][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:15]2)=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][NH:11][C:12]=2[N:13]=1

Participants

3

Reactant 2

HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 1180366867-(Dimethoxymethyl)-1,2,3,4-tetrahydro-6-(tetrahydro-2H-pyran-4-yl)-1,8-naphthyridine

Product 1

HCID 118036780Tert-butyl 4-(2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)piperidine-1-carboxylate

Procedure

The title compound was synthesized in an analogous manner to intermediate 312 by replacing 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate. The title compound was obtained as a white foam. (UPLC-MS 3) tR 0.80 min; ESI-MS 392.3 [M+H]+.

Sources & evidence

ORD record
ord-c74b0658d0b44afca748f0d5a74ba60f
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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