Lithium borohydride → 4-Cyclopropyl-6-hydroxymethyl-1,4-dihydro-quinoline-3-carbonitrile

HRID 1297691Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2[CH:18]1[CH2:20][CH2:19]1)=O)C.[BH4-].[Li+]>>[CH:18]1([CH:9]2[C:8]3[C:13](=[CH:14][CH:15]=[C:6]([CH2:4][OH:3])[CH:7]=3)[NH:12][CH:11]=[C:10]2[C:16]#[N:17])[CH2:19][CH2:20]1

Participants

Reactant 2

HCID 4148881Lithium borohydride

HCID 58585833HCID 58585833, compound

Product 1

HCID 585857844-Cyclopropyl-6-hydroxymethyl-1,4-dihydro-quinoline-3-carbonitrile

Procedure

Similar procedure as described in example 46e was used, starting from 3-cyano-4-cyclopropyl-quinoline-6-carboxylic acid ethyl ester (example 57a) and lithium borohydride to give 4-cyclopropyl-6-hydroxymethyl-1,4-dihydro-quinoline-3-carbonitrile as a yellow solid. LC-MS m/e 227 (MH+).

Sources & evidence

ORD record: ord-86e0ae3571864844ac6331b4ad45d1eb
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250515B2

Reaction notes

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