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

HRID 1954677

反応式

HRID 1954677 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 NaOH and benzyl chloroformate (5.5 mL, 38.7 mmol) was added dropwise and the pH maintained at 9.5 with 2N NaOH. The reaction was stirred for an additional 1 hour at room temperature. The organic solvent was evaporated in vacuo, and diethyl ether (100 mL) and water (50 mL) were added to the residue. The aqueous layer was separated, the pH of the aqueous solution was adjusted to 2.8 with 3N HCl, and ethyl acetate (150 mL) was added. The organic layer was separated and dried (MgSO4) and 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, and diethyl ether (100 mL) and water (50 mL)
  3. additionwere added to the residue
  4. customThe aqueous layer was 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-562908c1f98b4860998d2ec81c0eb866
出典データセット
uspto-grants-2000_09
特許番号
US06124277

関連ノート

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