Tetrahydrofuran → HCID 59745553, compound

HRID 2080542Notes

Reaction equation

HRID 2080542 reaction equation
[CH2:1]([NH:3][C:4](=[O:31])[CH2:5][N:6]1[CH2:11][CH2:10][C@H:9]2[CH2:12][C@@H:13]([C:26]([O:28]CC)=[O:27])[N:14]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C@H:8]2[CH2:7]1)[CH3:2].C1COCC1.O.[OH-].[Li+]>O>[CH2:1]([NH:3][C:4](=[O:31])[CH2:5][N:6]1[CH2:11][CH2:10][C@H:9]2[CH2:12][C@@H:13]([C:26]([OH:28])=[O:27])[N:14]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C@H:8]2[CH2:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59745556HCID 59745556, compound

Product 1

HCID 59745553HCID 59745553, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl rel-(2S,3aS,7aR)-6-[2-(ethylamino)-2-oxoethyl]-1-[(4-methoxyphenyl)sulfonyl]octahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate under step a) (62 mg, 0.13 mmol) was made in 1:1 THF:H2O (20 vols). Lithium hydroxide monohydrate (65.5 mg, 1.56 mmol) was added and the reaction stirred at room temperature for 18 hours. The THF was removed in vacuo, and the aqueous layer extracted with EtOAc (3×10 mL). The organic extracts were collected, dried over magnesium sulfate and filtered. The solvent was then removed in vacuo, before being placed on a high vacuum line for 2 hours. The product was used in the next step with no further purification.

Workup

  1. customThe THF was removed in vacuo
  2. extractionthe aqueous layer extracted with EtOAc (3×10 mL)
  3. customThe organic extracts were collected
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then removed in vacuo
  7. waitbefore being placed on a high vacuum line for 2 hours
  8. customThe product was used in the next step with no further purification

Sources & evidence

ORD record
ord-2c6eadeaad9b4c9585216ad014953021
Source dataset
uspto-grants-2011_04
Patent number
US07932389B2

Reaction notes

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