Acetic Acid → HCID 178453993, compound

HRID 706895Notes

Reaction equation

HRID 706895 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 3A (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-b80741d594fa4927a77f5c0ff8b72284
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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