Methanol → Methyl 3-((1,1-Dimethylethylsulfinamido)methyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate

HRID 1411893ノート

反応式

HRID 1411893 の反応式
[C:1]([S:5](/[N:7]=[CH:8]/[C:9]1[N:17]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])=[O:6])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO>O>[CH3:3][C:1]([CH3:4])([S:5]([NH:7][CH2:8][C:9]1[N:17]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])=[O:6])[CH3:2]

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 89548949methyl 3-[(E)-tert-butylsulfinyliminomethyl]-5,6,7,8-tetrahydroindolizine-2-carboxylate

生成物 1

HCID 86684449Methyl 3-((1,1-Dimethylethylsulfinamido)methyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate収率 97.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 238a (4.0 g, 12.8 mmol, 1.0 eq.), NaBH4 (2.9 g, 76.9 mmol, 6.0 eq.), and methanol (100 mL). The reaction mixture was stirred at room temperature for 1 h. After this time water (50 mL) was added to the reaction and the resulting mixture was concentrated under reduced pressure. The residue was extracted with dichloromethane (3×50 mL). The combined organic layer was evaporated under reduced pressure to afford 238b (3.9 g, 96%), which was directly used in next step without further purification. MS: [M-C4H10NOS]+ 192.3.

後処理

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (3×50 mL)
  4. customThe combined organic layer was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-1f24d03850c54fa0a86a77977d65b9a8
出典データセット
uspto-grants-2014_12
特許番号
US08921353B2

反応ノート

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