Acetic Acid → HCID 86679529, compound

HRID 1776573Notes

Reaction equation

HRID 1776573 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]([C:10]([O:12][CH2:13][C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[O:11])=[CH:8][C:7]=2[CH:26]=O)[CH2:3][CH2:2]1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]([C:10]([O:12][CH2:13][C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])=[O:11])=[CH:8][C:7]=2[CH2:26][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 866795282-(Benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoate

Product 1

HCID 86679529HCID 86679529, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoate (3.73 g, 10.13 mmol) and morpholine (1.15 g, 13.17 mmol) in dry THF (50 ml), under argon atmosphere, was stirred for 15 minutes at RT. Na(OAc)3BH (2.79 g, 13.17 mmol) and CH3COOH (754 μl, 13.17 mmol) were added. CH3COOH was added to reach a pH between 5 and 6. The mixture stirred at RT for 24 hours. The solvent was removed, and the crude was dissolved in EtOAc and washed with NaHCO3 sat. sol. and brine. The organic phase was dried over Na2SO4, and the solvent was removed to give 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-(morpholinomethyl)benzoate (4.45 g, quantitative yield).

Workup

  1. customThe solvent was removed
  2. dissolutionthe crude was dissolved in EtOAc
  3. washwashed with NaHCO3 sat. sol. and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-8f22cf2589b74c1693b6a7780c354d28
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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