Ammonium Chloride → HCID 66615727, compound

HRID 333581Notes

Reaction equation

HRID 333581 reaction equation
[CH3:1][C@@H:2]1[C@H:11]2[C:5](=[C:6]([CH3:15])[CH2:7][CH2:8][C@@H:9]([C:12]([CH3:14])=[CH2:13])[CH2:10]2)[C:4](=[O:16])[CH2:3]1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[CH3:1][C@@H:2]1[C@H:11]2[C:5](=[C:6]([CH3:15])[CH2:7][CH2:8][C@@H:9]([C:12]([CH3:14])=[CH2:13])[CH2:10]2)[C@H:4]([OH:16])[CH2:3]1.[CH3:1][C@@H:2]1[C@H:11]2[C:5](=[C:6]([CH3:15])[CH2:7][CH2:8][C@@H:9]([C:12]([CH3:14])=[CH2:13])[CH2:10]2)[C@@H:4]([OH:16])[CH2:3]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 66615637HCID 66615637, compound

Product 2

HCID 14779596HCID 14779596, compoundYield 2%HCID 66615727HCID 66615727, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

At −10° C., a mixture of (3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-3,3a,4,5,6,7-hexahydroazulen-1(2H)-one (53 mg, 0.243 mmol) and CeCl3.7H2O (90 mg, 0.243 mmol) in MeOH (5 ml) was treated with sodium borohydride (9.2 mg, 0.243 mg) and the resulting mixture was stirred at 0° C. for 20 min., poured into aqueous saturated NH4Cl solution (5 ml) and ice and extracted twice with diethyl ether (3 ml). The combined organic phases were washed with aqueous saturated NaHCO3 solution (3 ml), with aqueous saturated NaCl solution (3 ml), dried with MgSO4, filtered, and the solvent evaporated. FC (5 g SiO2, hexane/MTBE 10:0.1 to 10:0.2 to 10:0.5) of the crude product (52 mg, GC: 93:7 (1R)/(1S)-epimer) gave (1R,3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol (34 mg, 64%) and (1 S,3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol (1 mg, 2%).

Workup

  1. extractionextracted twice with diethyl ether (3 ml)
  2. washThe combined organic phases were washed with aqueous saturated NaHCO3 solution (3 ml), with aqueous saturated NaCl solution (3 ml)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-a15e3a68dceb434d8b05cef64b3d6bf6
Source dataset
uspto-grants-2014_11
Patent number
US08883468B2

Reaction notes

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