4-Fluorobenzaldehyde → HCID 69066592, compound

HRID 731240Notes

Reaction equation

HRID 731240 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[NH2:13])=[O:4].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[NH:13][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([F:14])=[CH:16][CH:17]=1)=[O:4]

Participants

7

Reactant 4

HCID 680234-FluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 11615492cis-2-amino-cyclooctanecarboxylic acid methyl ester

Product 1

HCID 69066592HCID 69066592, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

cis-2-Amino-cyclooctanecarboxylic acid methyl ester (0.66 g, 3.56 mmol) was dissolved in methanol (20 mL). 4-Fluoro-benzaldehyde (0.44 g, 3.56 mmol) was added followed by acetic acid (1 mL). The solution was stirred at 25° C. for 10 min. Sodium cyanoborohydride (0.56 g, 8.9 mmol) was added and the mixture was stirred at 25° C. for 16 h. The mixture was poured into 1/2 saturated aqueous sodium bicarbonate solution (150 mL). The aqueous layer was extracted with ethyl acetate (2×150 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the crude product, cis-2-(4-fluoro-benzylamino)-cyclooctanecarboxylic acid methyl ester (0.7 g, 2.39 mmol, 67%), as a clear oil. LC-MS (ESI) calcd for C17H24FNO2 293.18, found 294.3 [M+H+].

Workup

  1. stirringthe mixture was stirred at 25° C. for 16 h
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×150 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb566d5add0b4cd3a3ede2cb7998f370
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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