(S)-6-(tert-Butoxycarbonyl)-7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylic acid → (7S)-6-(tert-butoxycarbonyl)-7-isopropyl-5-methyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylic acid

HRID 1777832Notes

Reaction equation

HRID 1777832 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=2)[C@@H:9]1[CH:20]([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:24]1C=C2C(C)N(C(OC(C)(C)C)=O)[C@@H](C(C)C)C2=NC=1>>[C:1]([O:5][C:6]([N:8]1[CH:16]([CH3:24])[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=2)[C@@H:9]1[CH:20]([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 118274906(S)-6-(tert-Butoxycarbonyl)-7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylic acidHCID 118274936Tert-butyl (7S)-3-chloro-7-isopropyl-5-methyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate

Product 1

HCID 118274884(7S)-6-(tert-butoxycarbonyl)-7-isopropyl-5-methyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylic acid

Procedure

Procedure same as that for (S)-6-(tert-butoxycarbonyl)-7-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxylic acid, using tert-butyl(7S)-3-chloro-7-isopropyl-5-methyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate as a starting material. LC-MS tR=0.99 min in 1 min chromatography, MS (ESI) m/z 321.5 [M+H]+.

Sources & evidence

ORD record
ord-afc73c962cf74326a32be8b709dd11ec
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

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