Acetic Acid → HCID 178453993, compound

HRID 2167985Notes

Reaction equation

HRID 2167985 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-c7cf2b31844a48be930b43f74a308e59
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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