Sodium borohydride → HCID 12082825, compound

HRID 1274297Notes

Reaction equation

HRID 1274297 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-0084969a416141bda35783502751577b
Source dataset
uspto-grants-2000_12
Patent number
US06156781

Reaction notes

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