Sodium borohydride → tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamate

HRID 451843ノート

反応式

HRID 451843 の反応式
[CH2:1]([C@H:4]1[C:8](=[O:9])[N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:6]([C:17](OCC)=[O:18])[CH2:5]1)[CH:2]=[CH2:3].[BH4-].[Na+]>CO.O>[OH:18][CH2:17][C@@H:6]([NH:7][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:5][C@H:4]([CH2:8][OH:9])[CH2:1][CH:2]=[CH2:3]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 5287387(2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate

生成物 1

HCID 58011569tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamate収率 85%

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

実験手順

To a solution of (2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate (30 g, 0.1 mol) in MeOH/H2O (700/70 mL) was added NaBH4 (25 g, 0.66 mol), the result mixture was stirred 1 hr at rt and quenched with sat. aq. NH4Cl (300 mL). The organic solvent was removed under vacuum and extracted with EtOAc (3×250 mL). The combined organic phases were washed with brine (250 mL) and dried over anhydrous Na2SO4, filtered and evaporated to afford crude tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (22 g, 85%). It was used in the next step without further purification.

後処理

  1. customquenched with sat. aq. NH4Cl (300 mL)
  2. customThe organic solvent was removed under vacuum
  3. extractionextracted with EtOAc (3×250 mL)
  4. washThe combined organic phases were washed with brine (250 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-91dc0d462e744edcb9d8a9869fe7742b
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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