Acetic Acid → HCID 57671205, compound

HRID 731325Notes

Reaction equation

HRID 731325 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[NH2:11])=[O:4].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[NH:11][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11008182(1S,2R)-Methyl 2-aminocyclohexanecarboxylate

Product 1

HCID 57671205HCID 57671205, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

The crude (1S,2R)-2-amino-cyclohexanecarboxylic acid methyl ester (4.97 mmol) was dissolved in methanol (15 mL) at 25° C. and 4-fluorobenzaldehyde (0.533 mL, 4.97 mmol), glacial acetic acid (1 mL) and sodium cyanoborohydride (0.781 g, 12.4 mmol) were added sequentially. The reaction mixture was stirred at 25° C. for 19 h, and then was partitioned between saturated sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL). The combined organic layers were dried over sodium sulfate, decanted, and were concentrated in vacuo to afford the crude product, (1S,2R)-2-(4-fluoro-benzylamino)-cyclohexanecarboxylic acid methyl ester as a yellow oil, which was used directly in the next step without further purification.

Workup

  1. customwas partitioned between saturated sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customdecanted
  4. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-6d1af6bfd9ce48c0b0f42668b38d96bf
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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