Acetic Anhydride → HCID 22840849, compound

HRID 2081971Notes

Reaction equation

HRID 2081971 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:19])[CH:7]=[C:8]2[C:12]=1[N:11]([CH3:13])[C@H:10]1[N:14]([CH3:17])[CH2:15][CH2:16][C@@:9]21[CH3:18])([O-])=O.[C:20](OC(=O)C)(=[O:22])[CH3:21].[H][H]>[Pt].O1CCCC1>[C:20]([NH:1][C:4]1[CH:5]=[C:6]([OH:19])[CH:7]=[C:8]2[C:12]=1[N:11]([CH3:13])[C@H:10]1[N:14]([CH3:17])[CH2:15][CH2:16][C@@:9]21[CH3:18])(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14349820(3 aS-cis)-1,2,3,3a,8,8a-hexahydro-7-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-olHCID 178418361HCID 178418361, compound

Product 1

HCID 22840849HCID 22840849, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A Parr hydrogenation bottle is charged with 3.20 g of (3aS-cis)-1,2,3,3a,8,8a-hexahydro-7-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol, methyl carbamate ester, 0.3 g of 1% platinum-on-carbon catalyst, 1.53 g of acetic anhydride and 50 ml of degassed tetrahydrofuran. The mixture is shaken at room temperature under an initial hydrogen pressure of 40 psi (pounds per square inch) until uptake of hydrogen ceases. The catalyst is removed by filtration and the filtrate is concentrated in vacuo to afford (3aS-cis)-7-acetylamino-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol, methyl carbamate ester.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-bcc7872f7a36426380d1ad0fc27ef2f4
Source dataset
uspto-grants-1993_02
Patent number
US05187165

Reaction notes

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