Sodium cyanoborohydride → HCID 86699878, compound

HRID 241507Notes

Reaction equation

HRID 241507 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH:5]1[F:15].C([BH3-])#N.[Na+]>C(O)(=O)C>[F:15][CH:5]1[CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:4]1[NH:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 123639140HCID 123639140, compound

Product 1

HCID 86699878HCID 86699878, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of crude 6-fluoro-6,7,8,9-tetrahydrobenzocylohepten-5-one-O-methyl-oxime E/Z-mixture (1.23 g; 5.95 mmol) prepared as described in example P2a in acetic acid (12 ml) was added portion wise sodium cyanoborohydride 95% (0.75 g; 11.9 mmol) at 15° C. The mixture was stirred for 6 hours at 23° C. Most of acetic acid was removed under reduced pressure. The residue was poured in 2N NaOH (50 ml) and was extracted with ethylacetate (3×30 ml). Combined organics were dried over sodium sulfate and solvent was removed in vacuo. The crude (1.45 g) was subject to flash chromatography (eluant: c-hexane/ethyl acetate 100:0 to 0:100) to afford 0.645 g (52% of theory) of N-(6-fluoro-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-O-methyl-hydroxylamine as a yellow oil.

Workup

  1. customMost of acetic acid was removed under reduced pressure
  2. additionThe residue was poured in 2N NaOH (50 ml)
  3. extractionwas extracted with ethylacetate (3×30 ml)
  4. dry with materialCombined organics were dried over sodium sulfate and solvent
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-93bf242e0342426e85d0be6f80935841
Source dataset
uspto-grants-2014_02
Patent number
US08653003B2

Reaction notes

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