Sodium cyanoborohydride → N-(7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-O-methyl-hydroxylamine

HRID 241504Notes

Reaction equation

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

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of crude 7-chloro-3,4-dihydro-2H-naphthalen-1-one-O-methyl-oxime (5.9 g; 28.14 mmol) prepared as described in example P1a in acetic acid (100 ml) was added portion wise sodium cyanoborohydride 95% (3.54 g; 56.3 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 (100 ml) and was extracted with ethylacetate (3×80 ml). Combined organics were dried over sodium sulfate and solvent was removed in vacuo. The crude (8.2 g) was subject to flash chromatography (eluant: c-hexane/ethyl acetate 90:10) to afford 2.70 g (45% of theory) of N-(7-chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-O-methyl-hydroxylamine as a yellow oil.

Workup

customMost of acetic acid was removed under reduced pressure
additionThe residue was poured in 2N NaOH (100 ml)
extractionwas extracted with ethylacetate (3×80 ml)
dry with materialCombined organics were dried over sodium sulfate and solvent
customwas removed in vacuo

Sources & evidence

ORD record: ord-63d813b5c6dd47a19ca7e2e31b7fcb3b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653003B2

Reaction notes

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