Ammonia → HCID 90387811, compound

HRID 2201732Notes

Reaction equation

HRID 2201732 reaction equation
N.[Li].[CH3:3][C@@:4]12[CH2:17][CH2:16][C:15](=[O:18])[CH:14]=[C:13]1[CH2:12][CH2:11][C@H:10]1[C@H:5]2[CH2:6][C@@H:7]2[CH2:21][CH2:20][C@H:19]([OH:22])[C@@:8]2([CH3:23])[CH2:9]1.[NH4+].[Cl-]>C1COCC1>[CH3:3][C@@:4]12[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][C@H:13]1[CH2:12][CH2:11][C@H:10]1[C@H:5]2[CH2:6][C@@H:7]2[CH2:21][CH2:20][C@H:19]([OH:22])[C@@:8]2([CH3:23])[CH2:9]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium Chloride2×HCID 3028194LithiumHCID 90388341HCID 90388341, compound

Product 1

HCID 90387811HCID 90387811, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A three-neck flask equipped with a dry ice condenser was cooled to −78° C. and anhydrous ammonia (100 mL) was condensed into the flask. Lithium (134 mg, 19 mmol, 10 equiv) was added, and the resulting blue solution was stirred for 0.5 h. To this was added a solution of compound 19 (550 g, 1.91 mmol) in dry THF (50 mL). After 3 h of stirring, solid NH4Cl was added until the blue color disappeared, and the reaction mixture was allowed to warm to room temperature overnight and aqueous NH4Cl was added. The product was extracted into EtOAc (100 mL×3), and the combined organic extracts were washed with brine, dried and the solvent evaporated. Column chromatography (silica gel eluted with 10% EtOAc in hexanes) gave compound (480 mg, 87%) as a colorless oil: 1H NMR (CDCl3) δ 3.63 (t, J=7.8 Hz, 1H), 0.98 (s, 3H), 0.72 (s, 3H); 13C NMR (CDCl3) δ 212.0, 81.5, 54.0, 46.6, 45.0, 44.5, 43.0, 38.2, 37.9, 35.8, 34.6, 31.8, 30.3, 29.1, 25.5, 24.7, 11.4, 11.1; IR νmax 3416, 1709 cm−1.

Workup

  1. customA three-neck flask equipped with a dry ice condenser
  2. customcondensed into the flask
  3. stirringAfter 3 h of stirring
  4. temperatureto warm to room temperature overnight
  5. extractionThe product was extracted into EtOAc (100 mL×3)
  6. washthe combined organic extracts were washed with brine
  7. customdried
  8. customthe solvent evaporated
  9. washColumn chromatography (silica gel eluted with 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-98dc7ff2bfb8463f8480591f4354b77c
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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