Acetic Acid → HCID 14371634, compound

HRID 1464007Notes

Reaction equation

HRID 1464007 reaction equation
[CH3:1][O:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][C@@H:9]3[CH2:13][C:14]4[C:19]([C@H:8]3[C:7]=2[CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4.C=O.[C:24]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[CH3:1][O:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([CH3:24])[C@@H:9]3[CH2:13][C:14]4[C:19]([C@H:8]3[C:7]=2[CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 14371630HCID 14371630, compound

Product 1

HCID 14371634HCID 14371634, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 300 mg (1.00 mmol) of Compound P from step E was dissolved in 20 mL acetonitrile and 0.40 mL (5.3 mmol) 37% aqueous formaldehyde was added followed by 0.10 grams (1.59 mmol) sodium cyanoborohydride. After 30 minutes, the solution was brought to pH 7 by dropwise addition of glacial acetic acid then stirred an additional 1 hour and 45 minutes. The solvent was removed under reduced pressure, and the residue was taken up into 125 mL ethyl acetate. This was washed with 50 mL 10% sodium bicarbonate, dried (MgSO4) and evaporated to give an oil, which was purified by flash chromatography over silica gel, eluting with ethyl acetate to give 150 mg of trans-5,6,7,7a,8,12b-hexahydro-2-methoxy-3-chloro-7-methyl-benz[d]indeno[2,1-b]azepine (Compound Q) as an oil, 200 MHz NMR (CDCl3) d 2.17(dd,1H,J=12,Hz), 2.69(m,2H) 2.37(s,3H), 2.90-3.40(m,4H), 3.77(s,3H), 4.67(d,1H,J=9 Hz), 7.03(s,1H), 7.17(s,1H), 7.20-7.35(m,4H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washThis was washed with 50 mL 10% sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oil, which
  6. customwas purified by flash chromatography over silica gel
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5f169972cbea4ea6b34e5564021e31d3
Source dataset
uspto-grants-1994_04
Patent number
US05302716

Reaction notes

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