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

HRID 2055191Notes

Reaction equation

HRID 2055191 reaction equation
[CH2:1]([O:8][N:9]=[CH:10][C:11]1([C:18]([OH:20])=[O:19])[CH2:17][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.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][NH:9][CH2:10][C:11]1([C:18]([OH:20])=[O:19])[CH2:17][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

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 714169801-{[(Benzyloxy)imino]methyl}cycloheptane-1-carboxylic acid

Product 1

HCID 714169791-{[(Benzyloxy)amino]methyl}cycloheptane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(benzyloxyimino-methyl)-cycloheptanecarboxylic acid (4.44 g, 16.1 mmol) in methanol (200 mL) at 0° C. under an argon 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 (1.3 g, 20.9 mmol) was added portionwise alternately with methanolic HCl to maintain the red color. The reaction mixture was maintained at 0° C. for an additional 2 h and the volatiles were removed in vacuo to yield the title compound that was used without further purification. MH+278.

Workup

  1. temperatureto maintain the red color
  2. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-5fb8aec2745640ba8eaed9cfc31a408a
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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