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Water → rel-Phenylmethyl (3R,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate

HRID 81349
ノート
印刷プレビュー

反応式

HRID 81349 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][C@@H:10]1[OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:28]OS(OC)(=O)=O.O>C1COCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][C@H:10]1[O:25][CH3:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 58303445Phenylmethyl (3S,4S)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxy-1-piperidinecarboxylate

生成物 1

HCID 58522570rel-Phenylmethyl (3R,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate

試薬・触媒・溶媒 2

HCID 66133
Benzyl triethylammonium chloride
触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

benzyl (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-piperidine-1-carboxylate (5.00 g) is dissolved in THF (6 mL) and combined with 30 mL aqueous, semiconcentrated NaOH solution, benzyltriethylammonium chloride as well as dimethylsulphate (2.26 mL). After 22 h H2O (200 mL) is added and the mixture is extracted with EtOAc (150 mL). The organic phase is dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo. Purification is carried out using a silica gel column (cHex/EtOAc 65/35).

後処理

  1. extractionthe mixture is extracted with EtOAc (150 mL)
  2. customThe organic phase is dried on magnesium sulphate
  3. filtrationfiltered off from the desiccant and the solvent
  4. customPurification

出典と根拠

ORDレコード
ord-4ced7a16961f4e099f0f5614f0aa8edc
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846689B2

反応ノート

読み込み中…

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