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Sodium triacetoxyborohydride → HCID 68676597, Verbindung

HRID 1158511
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1158511
[CH2:1]([C@@:8]([OH:28])([C:12]([N:14]1[C@H:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[CH2:25][C@H:17]2[O:16][C:15]1([CH3:27])[CH3:26])=[O:13])[CH2:9][CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][O:30][C:31]([NH:33][C@H:34]([C:39]([NH:41][NH2:42])=[O:40])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:32].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[CH3:29][O:30][C:31](=[O:32])[NH:33][C@H:34]([C:39]([NH:41][NH:42][CH2:10][CH2:9][C@:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([OH:28])[C:12]([N:14]1[C@H:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[CH2:25][C@H:17]2[O:16][C:15]1([CH3:27])[CH3:26])=[O:13])=[O:40])[C:35]([CH3:38])([CH3:37])[CH3:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10679660[N-(methoxycarbony)-L-tert-leucinyl]hydrazineHCID 44819177HCID 44819177, Verbindung

Produkt 1

HCID 68676597HCID 68676597, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3 aH-indeno[1,2-d]oxazol-3-yl)-3-hydroxy-4-oxo-butyraldehyde (21h) (0.082 g, 0.21 mmol) and [N-(methoxycarbony)-L-tert-leucinyl]hydrazine (0.048 g, 0.23 mmol, prepared as reported JMC, 41, 3387, 1998) in dry THF (10 mL) was stirred for 3 h and [the LCMS (ESI+) shows 565 (M+)], then Na(OAc)3BH (0.137 g, 0.64 mmol) was added and stirred overnight. The reaction mixture was quenched with water and evaporated. The residue was dissolved in dichloromethane and washed with water, brine and dried. The crude product was analysed by LCMS (ESI+) which showed 567 (M+) the title compound with a minor quantity of the compound lacking the protection group on the indanol moiety [MS (ESI+): 527 (M+)]. This mixture was alkylated by the next step without purification.

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was quenched with water
  3. customevaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water, brine
  6. customdried
  7. customThis mixture was alkylated by the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-c9fb87735e8542d8873517f02b2081a3
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07807677B2

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