Ammonium Hydroxide → HCID 121396360, compound

HRID 60725Notes

Reaction equation

HRID 60725 reaction equation
[C:1]([O:9][CH:10]([C@H:12]1[O:21][C@H:15]2[O:16][C:17](C)(C)[O:18][C@H:14]2[CH2:13]1)[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+]>Cl>[C:1]([O:9][CH:10]([C@@H:12]1[CH2:13][C@H:14]([OH:18])[CH:15]([O:16][CH3:17])[O:21]1)[CH3:11])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 121396295HCID 121396295, compound2×

Product 1

HCID 121396360HCID 121396360, compoundYield 3.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethyl benzoate (compound 25h, 170 mg, 18 mmol) in the HCl solution (0.1N in MeOH, 3 mL) was stirred at room temperature overnight. The resulting mixture was neutralized by ammonium hydroxide and concentrated in vacuo. The residue was suspended in EtOAc and then filtered, the filtrate was concentrated in vacuo to afford 148 mg crude product of 1-[(2S,4S)-4-hydroxy-5-methoxy-tetrahydrofuran-2-yl]ethyl benzoate (compound 25i), which was used in the next step directly. MS obsd. (ESI+) [(M+H)+]: 267.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c47605789ec040e9a18a8fd9ba61c29a
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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