Acetic Acid → HCID 178453993, compound

HRID 624413Notes

Reaction equation

HRID 624413 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[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>[CH:23]1([N:1]([CH:17]2[CH2:16][CH2:31]2)[C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)[CH2:25][CH2:24]1

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 tert-butyl(trans)-4-aminocyclohexylcarbamate (1 g), molecular sieves 3A (1 g), acetic acid (2.67 mL), (1-ethoxycyclopropoxy)trimethylsilane (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 and concentrated. The residue was purified by flash chromotography (silica gel 80 g, 30-100% acetone/hexanes) providing the product.

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. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromotography (silica gel 80 g, 30-100% acetone/hexanes)
  9. customproviding the product

Sources & evidence

ORD record
ord-e2834afb7bd74297b81a1ef498da5d56
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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