Sodium borohydride → 4-Chloro-2-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinoline-6-methanol

HRID 540090Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][OH:13])[CH:10]=2)[N:5]=[C:4]([N:14]2[CH2:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17](=O)(=O)[CH2:16][CH2:15]2)[CH:3]=1.ClC1C2C(=CC=C(C(OC)=O)C=2)N=C(N2CC3C=CC=CC=3SCC2)C=1.[BH4-].[Na+]>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][OH:13])[CH:10]=2)[N:5]=[C:4]([N:14]2[CH2:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17][CH2:16][CH2:15]2)[CH:3]=1

Participants

Reactant 3

HCID 4311764Sodium borohydride

HCID 712544654-Chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinoline-6-methanol

HCID 71254493methyl 4-chloro-2-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinoline-6-carboxylate

Product 1

HCID 712545404-Chloro-2-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinoline-6-methanol

Procedure

The title compound was prepared in analogy to 4-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinoline-6-methanol in Example 3-23 in Scheme 5 by using methyl 4-chloro-2-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinoline-6-carboxylate (prepared in analogy to 4-(4-chloro-6-methylquinolin-2-yl)-8-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine in Example 1-1 in Scheme 4 by using methyl 2,4-dichloro quinoline-6-carboxylate and 2,3,4,5-tetrahydro-1,4-benzothiazepine) and sodium borohydride.

Sources & evidence

ORD record: ord-1c21f91ce95449e4802e81360960ac7d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

Loading…