Acetic Acid → HCID 54344576, compound

HRID 1651614Notes

Reaction equation

HRID 1651614 reaction equation
[CH3:1][N:2]1[C:6]2[CH2:7][CH2:8][C:9]3[C:16]4([CH3:19])[CH:17]([CH3:18])[CH:3]1[CH2:4][C:5]=2[C:10]=3[CH:11]=[CH:12][CH2:13][N:14]=[CH:15]4.C(O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>O>[CH3:1][N:2]1[C:6]2[CH2:7][CH2:8][C:9]3[C:16]4([CH3:19])[CH:17]([CH3:18])[CH:3]1[CH2:4][C:5]=2[C:10]=3[CH:11]=[CH:12][CH2:13][NH:14][CH2:15]4

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 54133654HCID 54133654, compound

Product 1

HCID 54344576HCID 54344576, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2.24 g of 1,2,3,4,5,6-hexahydro-3,6,12-trimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 23 ml of acetic acid, cooled to 15° C. under nitrogen, was added 1.70 g of sodium cyanoborohydride. The reaction mixture was stirred for an additional 2 hr and 90 ml of water was added. The solution was made basic (pH 12) with 50% aqueous sodium hydroxide solution and extracted with dichloromethane-ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered and concentrated. The residue was purified by flash chromatography (alumina, ether). Recrystallization from ether/pentane gave 1.55 g (69%) of product, mp 126°-128° C.

Workup

  1. extractionextracted with dichloromethane-ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (alumina, ether)
  7. customRecrystallization from ether/pentane

Sources & evidence

ORD record
ord-7873fa92064c45ec9dd8e243ddbc5bdc
Source dataset
uspto-grants-1990_05
Patent number
US04929622

Reaction notes

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