Isobutyl chloroformate → tert-Butyl ((1S,3R)-3-(hydroxymethyl)cyclohexyl)carbamate

HRID 1696208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696208
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15](O)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.[BH4-].[Na+].S([O-])(O)(=O)=O.[K+].C(=O)([O-])O.[Na+]>O1CCCC1.CO.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([CH2:15][OH:16])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

9

Edukt 5

HCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 2755995rel-(1R,3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclohexanecarboxylic acidHCID 4311764Sodium borohydride

Produkt 1

HCID 83823767tert-Butyl ((1S,3R)-3-(hydroxymethyl)cyclohexyl)carbamateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of cis-3-[(tert-butoxycarbonyl)amino]-cyclohexanecarboxylic acid (500 mg) in tetrahydrofuran (5 ml) was added triethylamine (344 μl) and isobutyl chloroformate (320 μl) under stirring at 0° C. After stirring at 0° C. for 1 hour, sodium borohydride (233 mg) was added, and methanol (5 ml) was added dropwise under stirring at 0° C. After stirring at 0° C. for 1 hour, 10% aqueous potassium hydrogen sulfate (10 ml) was added and neutralized with saturated aqueous sodium hydrogencarbonate. and extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with n-hexane:EtOAc=70:30 to 40:60 to give tert-butyl[cis-3-(hydroxymethyl)cyclohexyl]carbamate (311 mg) as a white powder.

Aufarbeitung

  1. stirringAfter stirring at 0° C. for 1 hour
  2. stirringunder stirring at 0° C
  3. stirringAfter stirring at 0° C. for 1 hour
  4. extractionand extracted with EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative thin layer chromatography on silica gel eluting with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-48d8f1b2730f496891bef545b99a27f6
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163767B2

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