Acetic Acid → HCID 178453993, compound

HRID 573136Notes

Reaction equation

HRID 573136 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)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 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-18098c36f9224e64b1842cccf356fc0a
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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