Acetic Acid → HCID 178453993, compound

HRID 1035905Notes

Reaction equation

HRID 1035905 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:16](O)(=O)[CH3:17].C(O[C:23]1(O[Si](C)(C)C)[CH2:25][CH2:24]1)C.[C:31]([BH3-])#N.[Na+]>CO>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([N:14]([CH:17]2[CH2:16][CH2:31]2)[CH:23]2[CH2:25][CH2:24]2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 178419079HCID 178419079, compound

Product 1

HCID 178453993HCID 178453993, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of trans-tert-butyl-4-aminocyclohexylcarbamate (1 g), molecular sieves 3 A (1 g), acetic acid (2.67 ml), (1-ethoxycyclopropoxy)trimethysilane (3.74 ml) and sodium cyanoborohydride (0.880 g) in dry methanol (10 ml) was heated at reflux for 3 hours. The insolubles were filtered off, the resulting solution was basified with aqueous NaOH (6 M) to pH 14, and extracted with ether. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (silica gel 80 g, 30-100% acetone/hexanes) to provide the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe insolubles were filtered off
  4. extractionextracted with ether
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (silica gel 80 g, 30-100% acetone/hexanes)

Sources & evidence

ORD record
ord-ec77b574a06e41cabe20a5c6c6343c54
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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