Ammonia → HCID 90388608, compound

HRID 2201740Notes

Reaction equation

HRID 2201740 reaction equation
N.[Li].[OH:3][C@H:4]1[C@:8]2([CH3:22])[CH2:9][C@H:10]3[C@H:19]([CH2:20][C@H:7]2[CH2:6][CH2:5]1)[C@@H:18]1[C:13](=[CH:14][C:15](=[O:21])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3.[NH4+].[Cl-]>C1COCC1>[OH:3][C@H:4]1[C@:8]2([CH3:22])[CH2:9][C@H:10]3[C@H:19]([CH2:20][C@H:7]2[CH2:6][CH2:5]1)[C@@H:18]1[C@H:13]([CH2:14][C:15](=[O:21])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 90388059HCID 90388059, compound

Product 1

HCID 90388608HCID 90388608, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A three-neck flask fitted with a dry ice condenser was cooled to −78° C., and anhydrous ammonia (100 mL) was condensed into the flask. Lithium (0.21 g, 30 mmol) was added, and the resulting blue solution was stirred for 0.5 h. To this was added a solution of compound 36 (820 mg, 3.0 mmol) in dry THF (30 mL). After 3 h, solid NH4Cl was added until the blue color disappeared. The cooling bath was removed and stirring was continued at room temperature overnight. Aqueous NH4Cl was added and the product was extracted into EtOAc (100 mL×3). The combined extracts were washed with brine, dried and the solvent evaporated. Flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) gave compound 37 (615 mg, 75%) as a white solid: [α]D25+52.3 (c 0.13, CHCl3); 1H NMR (CDCl3) δ 3.58 (t, J=7.7 Hz, 1H), 0.68 (s, 3H); 13C NMR (CDCl3) δ 211.7, 81.3, 48.3, 47.8, 45.7, 44.9, 44.5, 43.6, 42.9, 41.0, 37.8, 34.2, 33.7, 30.1, 29.9, 29.0, 25.3, 11.0; IR νmax 3419, 1713 cm−1. Anal. Calcd for (C18H28O2): C, 78.21; H, 10.21. Found: C, 78.29; H, 10.12.

Workup

  1. customA three-neck flask fitted with a dry ice condenser
  2. customcondensed into the flask
  3. waitAfter 3 h
  4. customThe cooling bath was removed
  5. stirringstirring
  6. waitwas continued at room temperature overnight
  7. additionAqueous NH4Cl was added
  8. extractionthe product was extracted into EtOAc (100 mL×3)
  9. washThe combined extracts were washed with brine
  10. customdried
  11. customthe solvent evaporated
  12. washFlash column chromatography (silica gel eluted with 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bedb14bc177c4aa69c85cf6e6c2fa6be
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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