Sodium borohydride → HCID 12082825, compound

HRID 2298402Notes

Reaction equation

HRID 2298402 reaction equation
[CH:1]([C:3]1[C:4]([C:24]([F:27])([F:26])[F:25])=[N:5][N:6]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[C:4]([C:24]([F:25])([F:27])[F:26])=[N:5][N:6]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:21])=[O:22])=[CH:16][CH:15]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12082824HCID 12082824, compound

Product 1

HCID 12082825HCID 12082825, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the aldehyde prepared in Step 2 (165 mg, 0.41 mmol) in methanol (3.5 mL) at 0° C. was added sodium borohydride (16 mg, 0.41 mmol). The reaction solution was kept at 0° C. for 2.5 hours. The reaction was quenched with the addition of an aqueous 1M KHSO4 solution (3 mL). The mixture was extracted with dichloromethane and the organic solution dried and concentrated. The residue was chromatographed on silica (1:1 hexane:ethyl acetate) to give the desired product (36 mg, 46%): m.p. 179-180° C.; 1H NMR d 7.91 (m, 2H), 7.53-7.40 (m, 5H), 6.75 (s, 2H), 4.53 (d, 2h, J=5.0 Hz), 4.30 (t, 1H, J=5.0 Hz).

Workup

  1. customThe reaction was quenched with the addition of an aqueous 1M KHSO4 solution (3 mL)
  2. extractionThe mixture was extracted with dichloromethane
  3. customthe organic solution dried
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica (1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-68ae62773b8a41faa01753f13c8483ec
Source dataset
uspto-grants-2002_12
Patent number
US06492411B1

Reaction notes

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