Sodium cyanoborohydride → HCID 23519155, compound

HRID 2181112Notes

Reaction equation

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

Participants

Reactant 2

HCID 5003444Sodium cyanoborohydride

HCID 74058497HCID 74058497, compound

Product 1

HCID 23519155HCID 23519155, compound

Procedure

Reduction of 4-(methoxyimino-methyl)-benzoic acid tert-butyl ester with sodium cyanoborohydride as described in the preparation of compound 1-B gave the title hydroxylamine as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8:2) (56% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.59 (9H, s, t-Bu), 3.49 (3H, s, OCH3), 4.09 (2H, s, NCH2), 7.41 (2H, d, J=8.6 Hz, aromatics), 7.96 (2H, d, J=8.6 Hz, aromatics). The hydrochloride salt was obtained as a white solid: mp 130-132° C. Anal. calcd for C13H19NO3—HCl: C, 57.04; H, 7.36; N, 5.12. Found: C, 56.90; H, 7.27; N, 5.00.

Sources & evidence

ORD record: ord-978ba5fd320749e5a699dba04b8f17b1
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890942B2

Reaction notes

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