Water → n-((s)-4-Chloro-9-(r,s)-hydroxy-1-methoxy-2-nitro-6,7,8,9-tetrahydro-5h-benzocyclohepten-7-yl)-acetamide

HRID 1041169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041169
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][C@H:9]([NH:13][C:14](=[O:16])[CH3:15])[CH2:8][C:7](=[O:17])[C:6]=2[C:5]([O:18][CH3:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][C@H:9]([NH:13][C:14](=[O:16])[CH3:15])[CH2:8][CH:7]([OH:17])[C:6]=2[C:5]([O:18][CH3:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 57853797N-((S)-4-Chloro-1-methoxy-2-nitro-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide

Produkt 1

HCID 131729599n-((s)-4-Chloro-9-(r,s)-hydroxy-1-methoxy-2-nitro-6,7,8,9-tetrahydro-5h-benzocyclohepten-7-yl)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

N-((S)-4-Chloro-1-methoxy-2-nitro-9-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide (100 mg; 0.3 mmol), of Example 632f, in Methanol (10 mL) was treated with Sodium tetrahydroborate (30 mg, 0.8 mmol) neat at rt. After 15 minutes, a second portion of Sodium tetrahydroborate (30 mg, 0.8 mmol) was added to the reaction mixture. After 30 minutes the reaction mixture was treated with water, then extract with Et2O followed by CH2Cl2 (2×). The aqueous phase was treated with 1N KOH and re-extracted with CH2Cl2. The organics were combined, dried over MgSO4, filtered and concentrated to give 210 mg (TW 100 mg) of whitish, crude N-((S)-4-Chloro-9-(R,S)-hydroxy-1-methoxy-2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-acetamide, which was used without further purification; MS (m/e) 328.97 (M+H).

Aufarbeitung

  1. extractionextract with Et2O
  2. additionThe aqueous phase was treated with 1N KOH
  3. extractionre-extracted with CH2Cl2
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e5ec667b3cb94fd98e527319691909fe
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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