Formaldehyde → tert-Butyl 5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 501749Notes

Reaction equation

HRID 501749 reaction equation
[CH2:1](O[C@H]1C2C(=CC(OCCC)=CC=2)[C@@H](N)C1)C=C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:33]1[CH:37]2[CH2:38][NH:39][CH2:40][CH:36]2[CH2:35][N:34]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].C=O.[OH-].[Na+]>ClCCCl>[CH3:1][N:39]1[CH2:38][CH:37]2[CH2:33][N:34]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][CH:36]2[CH2:40]1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 59418258tert-Butyl 5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Step BI (1): Sodium triacetoxyborohydride (666 mg, 3.14 mmol) was added to a magnetically stirred solution of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (165 mg, 0.777 mmol) and 37% formaldehyde (144 mg, 1.77 mmol) in 1,2-dichloroethane (10 mL). The resulting mixture was allowed to stir at rt for 16 h. Sodium hydroxide solution (2 mL of a 1 N solution) was added with vigorous stirring. Stirring was stopped and the layers were allowed to separate. The organic layer was removed and concentrated in vacuo with heating. Acetone was added to the residue, and the solution was decanted. The decanted portion was concentrated in vacuo to afford 80 mg (46% yield) of tert-butyl 5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate as a colorless oil.

Workup

  1. stirringStirring
  2. customto separate
  3. customThe organic layer was removed
  4. concentrationconcentrated in vacuo
  5. temperaturewith heating
  6. additionAcetone was added to the residue
  7. customthe solution was decanted
  8. concentrationThe decanted portion was concentrated in vacuo

Sources & evidence

ORD record
ord-bdce448522014d54a9ade4679291d6de
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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