Sodium hydride → (2S,4R)-N-Boc-4-(4-Bromobenzyloxy)-2-methyl-proline

HRID 49979

反応式

HRID 49979 の反応式
[H-].[Na+].C[O:4][C:5](=[O:20])[C@:6]1([CH3:19])[CH2:10][C@@H:9]([OH:11])[CH2:8][N:7]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1>C1COCC1.O>[C:12]([N:7]1[CH2:8][C@H:9]([O:11][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([Br:21])=[CH:23][CH:24]=2)[CH2:10][C@@:6]1([CH3:19])[C:5]([OH:4])=[O:20])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 106350101-(tert-Butyl) 2-methyl (2S,4R)-4-hydroxy-2-methylpyrrolidine-1,2-dicarboxylate

生成物 1

HCID 21301005(2S,4R)-N-Boc-4-(4-Bromobenzyloxy)-2-methyl-proline収率 28.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a suspension of sodium hydride (60% in oil) (0.12 g) (1.5 eq.) in 5 mL of dry THF was added (2S,4R)-N-Boc-4-hydroxy-2-methyl-proline methyl ester (0.55 g) in 5 mL of dry THF. The reaction mixture was stirred for 45 min., and a solution of 4-bromobenzyl bromide (0.75 g) (1.5 eq.) in 5 mL of dry THF was added. The reaction mixture was refluxed for 3 h. After cooling to RT, the reaction mixture was diluted with water and extracted with EtOAc. The aqueous layer was acidified and extracted with DCM. The combined organic extracts were washed with water, dried over MgSO4 and evaporated under reduced pressure to afford (2S,4R)-N-Boc-4-(4-bromo-benzyloxy)-2-methyl-proline (0.25 g).

後処理

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. extractionextracted with EtOAc
  3. extractionextracted with DCM
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-2d29d28f58b24fcfa52d6529402a7cce
出典データセット
uspto-grants-2004_03
特許番号
US06710064B2

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