Acetic Acid → HCID 21959504, compound

HRID 2109635Notes

Reaction equation

HRID 2109635 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)([CH3:6])[CH2:3][CH:4]=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>C1COCC1.[Zn]>[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)([CH3:6])[CH2:3][CH2:4][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 21959584HCID 21959584, compound

Product 1

HCID 21959504HCID 21959504, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of aldehyde (509 mg, 2.4 mmol, Step B) and morpholine (0.21 mL, 2.4 mmol) in THF (30 mL) was added NaBH(OAc)3 (0.73 g, 3.4 mmol). The mixture was stirred at RT overnight and washed with HCl (1 M). CH2Cl2 was added and the layers were separated. The aqueous layer was basified to pH 9 using NaOH 1M and extracted with CH2Cl2. The organic layer was dried and evaporated the nitro compound. To a solution of the nitro compound (0.50 g, 1.8 mmol) in THF (40 mL) was added AcOH (1.97 mmol, 34.5 mmol) followed by zinc (9.1 g, 137 mmol). The mixture was stirred for 1 h, filtered on Celite®, diluted with water and aqueous NaHCO3, and the THF layer was evaporated. The residue was extracted with EtOAc, dried and evaporated to give the title compound.

Workup

  1. washwashed with HCl (1 M)
  2. additionCH2Cl2 was added
  3. customthe layers were separated
  4. extractionextracted with CH2Cl2
  5. customThe organic layer was dried
  6. customevaporated the nitro compound
  7. stirringThe mixture was stirred for 1 h
  8. filtrationfiltered on Celite®
  9. additiondiluted with water and aqueous NaHCO3
  10. customthe THF layer was evaporated
  11. extractionThe residue was extracted with EtOAc
  12. customdried
  13. customevaporated

Sources & evidence

ORD record
ord-d8137398cb5c4654b8f30af4aa97fdb6
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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