tert-butyl (S)-3-chloro-7-isopropyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate → Tert-butyl (7S)-3-chloro-7-isopropyl-5-methyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate

HRID 1777831Notes

Reaction equation

HRID 1777831 reaction equation
ClC1C=C2CN(C(OC(C)(C)C)=O)[C@@H](C(C)C)C2=NC=1.CS(O[CH:26]([C:28]1[C:29]([C@@H:35]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH:36]([CH3:38])[CH3:37])=[N:30][CH:31]=[C:32]([Cl:34])[CH:33]=1)[CH3:27])(=O)=O>>[Cl:34][C:32]1[CH:33]=[C:28]2[CH:26]([CH3:27])[N:39]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@@H:35]([CH:36]([CH3:38])[CH3:37])[C:29]2=[N:30][CH:31]=1

Participants

3

Reactant 2

HCID 118274870tert-butyl (S)-3-chloro-7-isopropyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylateHCID 1182749161-(2-((S)-1-((tert-butoxycarbonyl)amino)-2-methylpropyl)-5-chloropyridin-3-yl)ethyl methanesulfonate

Product 1

HCID 118274936Tert-butyl (7S)-3-chloro-7-isopropyl-5-methyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate

Procedure

Procedure same as that for tert-butyl(S)-3-chloro-7-isopropyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate, using 1-(2-((S)-1-((tert-butoxycarbonyl)amino)-2-methylpropyl)-5-chloropyridin-3-yl)ethyl methanesulfonate as a starting material. LC-MS tR=1.12 min in 1 min chromatography, MS (ESI) m/z 311.4 [M+H]+. 1H NMR (CDCl3, 400 MHz, mixture of diastereomers): δ 8.43 (d, J=1.6 Hz, 1H), 7.52 (s, 0.7H), 7.46 (s, 0.3H), 5.05-5.00 (m, 1H), 4.94 (s, 0.3H), 4.81 (s, 0.7H), 2.88-2.39 (m, 0.3H), 2.32-2.08 (m, 0.7H), 1.55 (m, 3H), 1.44 (s, 9H), 1.26 (d, J=7.2 Hz, 0.9H), 1.09 (broad s, 2.1H), 0.81 (broad s, 2.1H), 0.48 (d, J=7.2 Hz, 0.9H).

Sources & evidence

ORD record
ord-16b7b96f8c034a5d870390efe39f0b9a
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

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