Hydrochloric Acid → 1-{[(Benzyloxy)amino]methyl}cyclohexane-1-carboxylic acid

HRID 2055174Notes

Reaction equation

[CH2:1]([O:8][N:9]=[CH:10][C:11]1([C:17]([OH:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl.CCC1(CC)C(=O)NC(=O)OC1.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][NH:9][CH2:10][C:11]1([C:17]([OH:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(benzyloxyimino-methyl)-cyclohexanecarboxylic acid (1.59 g, 6.08 mmol) in methanol (40 mL) at 0° C. under a nitrogen atmosphere was added a trace amount of methyl orange. A solution of saturated methanolic HCl was added until a persisten red color was observed. Sodium cyanoborohydride (0.42 g, 6.69 mmol) was added portionwise alternately with methanolic HCl to maintain the red color. The reaction mixture was maintained at 0° C. for an additional 3 h and the volatiles were removed in vacuo to yield the title compounds as a pale, yellow oil that was used without further purification. MH+264.

Workup

temperatureto maintain the red color
customthe volatiles were removed in vacuo

Sources & evidence

ORD record: ord-b849cd46e96c44b6996cc5eb23ae089c
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332485B2

Reaction notes

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