Benzyl chloroformate → (2R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid

HRID 726654

反応式

HRID 726654 の反応式
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O1CCCC1.O>[N:1]1([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4]

参加物

6

反応物 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2 回HCID 736316Pipecolic acid, (+)-

生成物 1

HCID 688346(2R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

D-hPro-OH (5.0 g, 38.7 mmol) was dissolved in tetrahydrofuran (100 mL) and water (30 mL). The pH of the solution was adjusted to 9.5 with 2N sodium hydroxide and benzyl chloroformate (5.5 mL, 38.7 mmol) was added dropwise and the pH maintained at 9.5 with 2N sodium hydroxide. The reaction was stirred for an additional 1 hour at room temperature. The organic solvent was evaporated in vacuo, diethyl ether (100 mL) and water (50 mL) was added to the residue. The aqueous layer separated, the pH of the solution was adjusted to 2.8 with 3N hydrochloric acid and ethyl acetate (150 mL) was added. The organic layer was separated and dried (MgSO4); the filtrate was concentrated in vacuo to give 9.6 g (95%) of a clear oil.

後処理

  1. additionwas added dropwise
  2. customThe organic solvent was evaporated in vacuo, diethyl ether (100 mL) and water (50 mL)
  3. additionwas added to the residue
  4. customThe aqueous layer separated
  5. additionwas added
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-e0b0eabec1134cad9b0eb027b09b8d26
出典データセット
uspto-grants-1998_01
特許番号
US05710130

関連ノート

読み込み中…