Sodium Bicarbonate → 2-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-hydroxymethyl-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17463

Reaktionsgleichung

Reaktionsgleichung von HRID 17463
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:24]#[N:25])[C:10]([CH3:23])=[C:11]([CH:21]=[O:22])[C:12]=3[N:13]3[CH2:17][CH2:16][C@H:15]([N:18]([CH3:20])[CH3:19])[CH2:14]3)[N:8]=2)[CH2:3][CH2:2]1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO.ClCCl>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:24]#[N:25])[C:10]([CH3:23])=[C:11]([CH2:21][OH:22])[C:12]=3[N:13]3[CH2:17][CH2:16][C@H:15]([N:18]([CH3:20])[CH3:19])[CH2:14]3)[N:8]=2)[CH2:2][CH2:3]1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2×HCID 866308522-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685869932-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-hydroxymethyl-5-methyl-1,3-benzoxazole-4-carbonitrileAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile (free form of #88) (120 mg, 0.35 mmol) was dissolved in methanol (2.4 ml) and dichloromethane (0.8 ml), then at 0° C., sodium borohydride (18 mg, 0.43 mmol) was added, followed by stirring at the same temperature for 1 hour. Next, at the same temperature, sodium borohydride (9 mg, 0.22 mmol) was further added, followed by stirring at the same temperature for 1 hour. An aqueous saturated sodium hydrogencarbonate solution was added, followed by farmer stirring for 5 minutes. The solution was extracted three times with chloroform. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (91 mg) as a roughly-purified product. This was washed with isopropyl ether to obtain the entitled compound (85 mg, 70%) as a white solid.

Aufarbeitung

  1. stirringby stirring at the same temperature for 1 hour
  2. stirringstirring for 5 minutes
  3. extractionThe solution was extracted three times with chloroform
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-f3a71063c91b448495867d1cb6763889
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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