Acetic Acid → HCID 178501211, compound

HRID 1422735Notes

Reaction equation

HRID 1422735 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([NH2:23])[CH2:19][CH2:18]1)=[O:16].C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCCl.CO>[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([NH:23][CH2:11][C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)[CH2:19][CH2:18]1)=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178501207HCID 178501207, compound

Product 1

HCID 178501211HCID 178501211, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

2,3-Dihydro-benzo[1,4]dioxine-6-carbaldehyde (198 mg, 1.21 mmol, 1.0 eq) is added at room temperature to a stirred solution of trans-4-amino-cyclohexanecarboxylic acid methyl ester (200 mg, 1.21 mmol, 1.0 eq) in 1,2-dichloroethane (8 mL) and methanol (2 mL), followed by acetic acid (80 μL, 1.39 mmol, 1.15 eq) and sodium cyanoborohydride (99 mg, 1.57 mmol, 1.3 eq). After 15 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×20 mL) and a saturated sodium hydrogen carbonate aqueous solution (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amino]-cyclohexanecarboxylic acid methyl ester as an orange oil (359 mg, 92% yield).

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5a0985de325b40cf9f4b38a77fd8ba04
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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