Hydrochloric Acid → HCID 78323073, compound

HRID 2201726Notes

Reaction equation

HRID 2201726 reaction equation
C1C(=O)N(Br)C(=[O:4])C1.CC([Si](C)(C)[O:14][C@@H:15]1[CH2:28][C@@H:27]2[C@H:18]([C@H:19]3[C@H:24]([CH2:25][CH2:26]2)[CH2:23][C@:22]2([CH3:34])[C:29](=[N:32][OH:33])[CH2:30][CH2:31][C@H:21]2[CH2:20]3)[CH2:17][CH2:16]1)(C)C.[BH4-].[Na+].Cl>O1CCOCC1>[CH3:34][C@@:22]12[C@@H:29]([N+:32]([O-:4])=[O:33])[CH2:30][CH2:31][C@H:21]1[CH2:20][C@@H:19]1[C@H:24]([CH2:25][CH2:26][C@H:27]3[C@H:18]1[CH2:17][CH2:16][C@H:15]([OH:14])[CH2:28]3)[CH2:23]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 4311764Sodium borohydrideHCID 131735721HCID 131735721, compound

Product 1

HCID 78323073HCID 78323073, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of NBS (210 mg, 1.3 mmol) in dioxane (4 mL) was added aqueous KHCO3 (260 mg, 2.6 mmol, 4 mL) at room temperature. The mixture was stirred for 30 min at room temperature. Compound 5 (105 mg, 0.26 mmol) in dioxane (10 mL) was added. The reaction was stirred for 14 h at room temperature and then NaBH4 was added (200 mg in 5 portions). The reaction was stirred for 3 h at room temperature. 6 N HCl (10 mL) was added and stirring at room temperature continued for 1 h. The product was extracted into EtOAc (50 mL×2). The combined extracts were dried, filtered, and removed. The residue was purified by flash column chromatography (silica gel eluted with 20% EtOAc in hexanes) to afford compound 6 (62 mg, 56%): mp 157-159° C.; [α]D20 +32.4 (c 0.21, CHCl3); 1H NMR (CDCl3) δ 4.40 (t, J=8.2 Hz, 1H), 4.05-4.10 (m, 1H), 2.56-2.51 (m, 1H), 0.73 (s, 3H); 13C NMR (CDCl3) δ 94.4, 66.3, 47.9, 47.2, 47.0, 45.8, 45.1, 40.4, 38.3, 36.1, 33.9, 33.8, 32.7, 28.4, 25.7, 24.6, 2.32, 12.1; IR νmax 3385, 2212, 1542 cm−1. Anal. Calcd for (C18H29NO3): C, 70.32; H, 9.51; N, 4.56. Found: C, 70.12; H, 9.32; N, 4.33.

Workup

  1. stirringThe reaction was stirred for 14 h at room temperature
  2. stirringThe reaction was stirred for 3 h at room temperature
  3. stirringstirring at room temperature
  4. waitcontinued for 1 h
  5. extractionThe product was extracted into EtOAc (50 mL×2)
  6. customThe combined extracts were dried
  7. filtrationfiltered
  8. customremoved
  9. customThe residue was purified by flash column chromatography (silica gel eluted with 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b0d2fc59b63f4323a9e4060a84479bae
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

Loading…