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

HRID 2055167Notes

Reaction equation

[CH2:1]([O:8][N:9]=[CH:10][C:11]1([C:16]([OH:18])=[O:17])[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.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][NH:9][CH2:10][C:11]1([C:16]([OH:18])=[O:17])[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)-cyclopentanecarboxylic acid (1.91 g, 7.72 mmol) in methanol (70 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 persistent red color was observed. Sodium cyanoborohydride (0.58 g, 9.27 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. The residue was purified by preparative reverse-phase HPLC to yield the title compound as a pale, yellow oil (1.1 g, 57%). MH+250.

Workup

temperatureto maintain the red color
customthe volatiles were removed in vacuo
customThe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-b2e50c1f09874cc78cc8bc55835f0f87
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332485B2

Reaction notes

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