Sodium cyanoborohydride → N-(3-iodo-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-O-methyl-hydroxylamine

HRID 241510Notes

Reaction equation

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

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of crude 3-iodo-6,7,8,9-tetrahydrobenzocylohepten-5-one-O-methyl-oxime E/Z-mixture (793 mg; 5.95 mmol) prepared as described in example P3b in acetic acid (5 ml) was added portion wise sodium cyanoborohydride 95% (0.63 g; 10.1 mmol) at 15° C. The mixture was stirred for 9 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 (840 mg) was subject to flash chromatography (eluant: c-hexane/ethyl acetate 100:0 to 10:90) to afford 88 mg (13% of theory) of N-(3-iodo-6,7,8,9-tetrahydro-5-H-benzocyclohepten-5-yl)-O-methyl-hydroxylamine in form of an oil.

Workup

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

Sources & evidence

ORD record: ord-07914ff27ab54e768fcb603ead247fde
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653003B2

Reaction notes

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