Dichloromethane → HCID 178469552, compound

HRID 23621Notes

Reaction equation

[CH:1]([C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][NH:6][C:5]=2[C:4]=1[CH3:18])=[O:2].C(Cl)Cl.[BH4-].[Na+]>CO>[OH:12][C:9]1[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:6]=[C:5]2[C:4]([CH3:18])=[C:3]([CH2:1][OH:2])[S:11][C:10]=12

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of ethyl 2-formyl-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (Preparation 3)(1.50 g, 5.66 mmol) in 1:1 CH2Cl2:MeOH (15 mL) was chilled in an ice bath before the addition of sodium borohydride (0.214 g, 5.66 mmol). The reaction was stirred at 0° C. for one hour and then quenched by the addition of water (30 mL). While continuing to chill in an ice bath, the mixture was adjusted to pH 4 by the careful addition of 1 N HCl. The resulting thick mixture was stirred at 0° C. for one hour before filtering. The collected solid was washed with water and dried in vacuo, affording the title compound (0.90 g) as an off-white solid. The filtrate was concentrated in vacuo to a volume of about 50 mL, more water was added, and the mixture was again filtered after chilling in ice, giving an additional 0.29 g of the title product.

Workup

customquenched by the addition of water (30 mL)
temperatureto chill in an ice bath
additionthe mixture was adjusted to pH 4 by the careful addition of 1 N HCl
stirringThe resulting thick mixture was stirred at 0° C. for one hour
filtrationbefore filtering
washThe collected solid was washed with water
customdried in vacuo

Sources & evidence

ORD record: ord-06d3f9e9c7164959ace2f8f6c2c9e567
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Reaction notes

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