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

HRID 501749ノート

反応式

HRID 501749 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bdce448522014d54a9ade4679291d6de
出典データセット
uspto-grants-2010_08
特許番号
US07772221B2

反応ノート

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