Acetic Acid → HCID 14552383, compound

HRID 654743Notes

Reaction equation

HRID 654743 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]=[C:7]([C:11]([O-:13])=[O:12])[CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:14](O)(=O)[CH3:15].[CH2:18](O)[CH3:19].[C:21]([BH3-])#[N:22].[Na+]>C1COCC1.O>[C:19]1([CH2:21][NH:22][CH:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH:7]2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:18]=[CH:7][CH:6]=[CH:5][CH:10]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 86746007HCID 86746007, compound

Product 1

HCID 14552383HCID 14552383, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 8-(phenylmethyl)amino]-1,4-dioxaspiro -[4.5]-dec-7-ene-7-carboxylate (395.4 g, 1.3 mole) and acetic acid (75.0 ml, 1.3 mole) were added to ethanol (4 1). Sodium cyanoborohydride (82.0 g, 1. mole) was added in portions over 3 hours. The mixture was stirred overnight, then poured into water. The pH was adjusted to 10, and the product was extracted with methylene chloride, which was then dried with sodium sulfate and evaporated to give a yellow oil having small clear lumps in it. This was dissolved in THF and poured through 3 inches of basic alumina, which was then rinsed well with THF. The filtrate was evaporated to give 397.2 g (99.9%) of the title product as a yellow-green oil.

Workup

  1. extractionthe product was extracted with methylene chloride, which
  2. dry with materialwas then dried with sodium sulfate
  3. customevaporated
  4. customto give a yellow oil
  5. additionpoured through 3 inches of basic alumina, which
  6. washwas then rinsed well with THF
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-c789352fc66546fab2e5b536659d8a91
Source dataset
uspto-grants-1992_07
Patent number
US05134143

Reaction notes

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