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

HRID 501749노트

반응식

HRID 501749 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bdce448522014d54a9ade4679291d6de
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772221B2

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