Acetic Acid → HCID 14552383, compound

HRID 1110774Notes

Reaction equation

HRID 1110774 reaction equation
[C:1]1([CH2:7][NH:8][C:9]2[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][C:10]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.C(O)C.C([BH3-])#N.[Na+]>C1COCC1.O>[C:1]1([CH2:7][NH:8][CH:9]2[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][CH:10]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 14552382HCID 14552382, 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 l). Sodium cyanoborohydride (82.0 g, 1.3 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-bf921e5be4914ce7bd7e1d73297fb7d9
Source dataset
uspto-grants-1990_12
Patent number
US04977160

Reaction notes

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